Abstract
An efficient mixed reagent for direct synthesis of symmetrical carboxylic anhydrides from carboxylic acids has been prepared. Carboxylic acids are converted to anhydrides using triphenylphosphine/ trichloroisocyanuric acid under mild reaction conditions at room temperature. Short reaction time, excellent yields of products, low cost, availability of reagents, simple experimental procedure, and easy work-up of the products are the main advantages of the presented method.
References
Adduci, J. M., & Ramirez, R. S. (1970). Anhydride formation with thionyl chloride. Organic Preparations and Procedures International, 2, 321-325. DOI: 10.1080/00304947009458638.10.1080/00304947009458638Search in Google Scholar
Akhlaghinia, B. (2004). Efficient conversion of tetrahydropyranyl (THP) ethers to their corresponding cyanides with triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/ n-Bu4NCN. Phosphorus, Sulfur, and Silicon and the Related Elements, 179, 1783-1786. DOI: 10.1080/10426500490466463.10.1080/10426500490466463Search in Google Scholar
Akhlaghinia, B., & Pourali, A. R. (2004). Novel and highly selective conversion of alcohols and thiols to alkyl nitrites with triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/ Bu4NNO2 system. Synthesis, 2004, 1747-1749. DOI: 10.1055 /s-2004-829122.10.1055/s-2004-829122Search in Google Scholar
Akhlaghinia, B. (2005a). Triphenylphosphine/2,3-dichloro-5,6- dicyanobenzoquinone in the presence of n-Bu4NN3 is a useful system for efficient conversion of tetrahydropyranyl (THP) ethers to their corresponding alkyl azides. Phosphorus, Sulfur, and Silicon and the Related Elements, 180, 1601-1604. DOI: 10.1080/104265090884292.10.1080/104265090884292Search in Google Scholar
Akhlaghinia, B. (2005b). A new and convenient method of generating alkyl isocyanates from alcohols, thiols and trimethylsilyl ethers using triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/Bu4NOCN. Synthesis, 2005, 1955-1958. DOI: 10.1055/s-2005-869906.10.1055/s-2005-869906Search in Google Scholar
Akhlaghinia, B., & Samiei, S. (2009). Triphenylphosphine/2,3- dichloro-5,6-dicyanobenzoquinone (DDQ)/[n-Bu4N]OCN as a useful system for the efficient conversion of tetrahydropyranyl (THP) ethers to the corresponding alkyl isocyanates. Phosphorus, Sulfur, and Silicon and the Related Elements, 184, 2525-2529. DOI: 10.1080/10426500802508212.10.1080/10426500802508212Search in Google Scholar
Akhlaghinia, B., & Rouhi-Saadabad, H. (2013). Direct and facile synthesis of acyl azides from carboxylic acids using the trichloroisocyanuric acid-triphenylphosphine system. Canadian Journal of Chemistry, 91, 181-185. DOI: 10.1139/cjc-2011-0493.10.1139/cjc-2011-0493Search in Google Scholar
Blankemeyer-Menge, B., Nimtz, M., & Frank, R. (1990). An efficient method for anchoring fmoc-anino acids to hydroxylfunctionalised solid supports. Tetrahedron Letters, 31, 1701-1704. DOI: 10.1016/s0040-4039(00)88858-9.10.1016/S0040-4039(00)88858-9Search in Google Scholar
Brady, W. T., & O’Neal, H. R. (1967). Further studies on the mechanism of diphenylketene cycloaddition. Journal of Organic Chemistry, 32, 2704-2702. DOI: 10.1021/jo01284a013. 10.1021/jo01284a013Search in Google Scholar
Bryson, T. A., & Roth, G. A., (1986). Synthetic studies directed at the B/C ring systems of CC-1065; preparation of substituted cyclopropyl indolenones. Tetrahedron Letters, 27, 3689-3692. DOI: 10.1016/s0040-4039(00)83854-x.10.1016/S0040-4039(00)83854-XSearch in Google Scholar
Burton, S. G., & Kaye, P. T. (1989). A convenient preparation of carboxylic acid anhydrides using a “supported” phosphorus pentoxide reagent. Synthetic Communications, 19, 3331-3335. DOI: 10.1080/00397918908052736.10.1080/00397918908052736Search in Google Scholar
Chen, F. M. F., & Benoiton, N. L. (1979). A general method for formylating sensitive amino acid esters. Synthesis, 1979, 709-710. DOI: 10.1055/s-1979-28805.10.1055/s-1979-28805Search in Google Scholar
Edman, J. R., & Simmons, H. E. (1968). Bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic anhydride. Journal of Organic Chemistry, 33, 3808-3816. DOI: 10.1021/jo01274a028.10.1021/jo01274a028Search in Google Scholar
Eglinton, G., & Jones, E. R. H., Shaw, B. L., & Whiting, M. C. (1954). Researches on acetylenic compounds. Part XLIII. A new method for the preparation of alkoxyacetylenes Journal of the Chemical Society, 1954, 1860-1865.Search in Google Scholar
Exner, O., & Jehlicka, E. (1970). Dipole moments and conformation of carboxylic acid anhydrides. Collection of Czechoslovak Chemical Communications, 35, 1514-1521. DOI: 10.1135/cccc19701514.10.1135/cccc19701514Search in Google Scholar
Fife, W. K., & Zhang, Z. D. (1986). Phase managed organic synthesis 3. Symmetrical anhydrides from carboxylic acids via polymer assisted reaction. Tetrahedron Letters, 27, 4937-4940. DOI: 10.1016/s0040-4039(00)85101-1.10.1016/S0040-4039(00)85101-1Search in Google Scholar
Fukuoka, S., Takimoto, S., Katsuki, T., & Yamaguchi, M. (1987). Activation of mixed carboxylic α-bromotoluoyl anhydrides by silver tetraflouroborate. Synthesis of ester and thiol esters. Tetrahedron Letters, 28, 4711-4712. DOI: 10.1016/s0040-4039(00)96605-x.10.1016/S0040-4039(00)96605-XSearch in Google Scholar
Funasaka, S., & Mukaiyama, T. (2008). A versatile, practical, and inexpensive reagent, pyridine-3-carboxylic anhydride (3- PCA), for condensation reactions. Bulletin of the Chemical Society of Japan, 81, 148-159. DOI: 10.1246/bcsj.81.148.10.1246/bcsj.81.148Search in Google Scholar
Hajipour, A. R., & Mazloumi, G. (2002). An efficient and simple procedure for preparation of esters and anhydrides from acid chlorides in the presence of 1,4-diazabicyclo[2.2.2]octane (dabco) under solvent-free conditions. Synthetic Communications, 32, 23-30. DOI: 10.1081/scc-120001504.10.1081/SCC-120001504Search in Google Scholar
Hata, T., Tajima, K., & Mukaiyama, T. (1968). A convenient method for the preparation of acid anhydrides from metallic carboxylates. Bulletin of the Chemical Society of Japan, 41, 2746-2747. DOI: 10.1246/bcsj.41.2746.10.1246/bcsj.41.2746Search in Google Scholar
Hiegel, G. A., Ramirez, J., & Barr, R. K. (1999). Chlorine substitution reactions using trichloroisocyanuric acid with triphenylphosphin. Synthetic Communications, 29, 1415-1419. DOI: 10.1080/00397919908086119.10.1080/00397919908086119Search in Google Scholar
Holzapfel, C. W., & Pettit, G. R. (1985). Antineoplastic agents. Part 108. Structural biochemistry. Part 23. Synthesis of the dolastatin thiazole amino acid component (gln)Thz. Journal of Organic Chemistry, 50, 2323-2327. DOI: 10.1021/jo00213a024.10.1021/jo00213a024Search in Google Scholar
Hu, Y. L., Wang, J. X., & Li, S. H. (1997). Synthesis of anhydrides fom acyl chlorides under ultrasound condition. Synthetic Communications, 27, 243-248. DOI: 10.1080/00397919708005024.10.1080/00397919708005024Search in Google Scholar
Hu, Y. L., Zhao, X. E., & Lu, M. (2011). Efficient and convenient synthesis of symmetrical carboxylic anhydrides from carboxylic acids with sulfated zirconia by phase transfer catalysis. Bulletin of the Chemical Society of Ethiopia, 25, 255-262. DOI: 10.4314/bcse.v25i2.65900.10.4314/bcse.v25i2.65900Search in Google Scholar
Hurd, C. D., & Thomas, C. L. (1933). The interaction of ketene with aromatic aldehydes and its bearing on the Perkin reaction. Journal of the American Chemical Society, 55, 275-283. DOI: 10.1021/ja01328a033.10.1021/ja01328a033Search in Google Scholar
Iranpoor, N., Firouzabadi, H., Akhlaghinia, B., & Azadi, R. (2004a). Conversion of alcohols, thiols, carboxylic acids, trimethylsilyl ethers, and carboxylates to thiocyanates with triphenylphosphine/diethylazodicarboxylate/NH4SCN. Synthesis, 2004, 92-96. DOI: 10.1055/s-2003-44369.10.1055/s-2003-44369Search in Google Scholar
Iranpoor, N., Firouzabadi, H., Akhlaghinia, B., & Nowrouzi, N. (2004b). Conversion of alcohols, thiols, and trimethysilyl ethers to alkyl cyanides using triphenylphosphine/2,3- dichloro-5,6-dicyanobenzoquinone/n-Bu4NCN. Journal of Organic Chemistry, 69, 2562-2564. DOI: 10.1021/jo035238v.10.1021/jo035238vSearch in Google Scholar
Iranpoor, N., Firouzabadi, H., Akhlaghinia, B., & Nowrouzi, N. (2004c). A novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the triphenylphosphine/ 2,3-dichloro-5,6-dicyanobenzoquinone(DDQ)/n- Bu4NN3 system. Tetrahedron Letters, 45, 3291-3294. DOI: 10.1016/j.tetlet.2004.02.141.10.1016/j.tetlet.2004.02.141Search in Google Scholar
Iranpoor, N., Firouzabadi, H., Azadi, R., & Akhlaghinia, B. (2005). Highly selective conversion of 1◦ and 2◦ tetrahydropyranyl ethers to thiocyanates and 3◦ ones to isothiocyanates using triphenylphosphine/diethyl azodicarboxylate/ NH4SCN. Journal of Sulfur Chemistry, 26, 133-137. DOI: 10.1080/17415990500135228.10.1080/17415990500135228Search in Google Scholar
Jenkins, J. A., & Cohen, J. (1975). Deuterium isotope effects and the influence of solvent in the redox and rearrangement reactions of 2-picoline N-oxide and phenylacetic anhydride. Journal of Organic Chemistry, 40, 3566-3571. DOI: 10.1021/jo00912a021.10.1021/jo00912a021Search in Google Scholar
Jorba, X., Albericio, F., Grandas, A., Bannwarth, W., & Giralt, E. (1990). Arenesulphonyltriazolides as condensing reagents in solid phasepeptide synthesis. Tetrahedron Letters, 31, 1915-1918. DOI: 10.1016/s0040-4039(90)80004-6.10.1016/S0040-4039(90)80004-6Search in Google Scholar
Kamiński, Z. J., Kolesi´nska, B., & Marcinkowska, M. (2004). Mild and efficient synthesis of carboxylic acid anhydrides from carboxylic acids and triazine coupling reagents. Synthetic Communications, 34, 3349-3358. DOI: 10.1081/scc-200030581.10.1081/SCC-200030581Search in Google Scholar
Karimi Zarchi, M. A., Mirjalili, B. F., Shamsi Kahrizsangi, Z., & Tayefi, M. (2010). A mild, clean, and simple synthesis of symmetrical carboxylic anhydrides from carboxylic acids using a polymer supported tosyl chloride. Journal of the Iranian Chemical Society, 7, 455-460. DOI: 10.1007/bf03246032.10.1007/BF03246032Search in Google Scholar
Katritzky, A. R., Shobana, N., Pernak, J., Afridi, A. S., & Fan, W. Q. (1992). Sulfonyl derivatives of benzotriazole: Part 1. A novel approach to the activation of carboxylic acids. Tetrahedron, 48, 7817-7822. DOI: 10.1016/s0040-4020(01)80459-2.10.1016/S0040-4020(01)80459-2Search in Google Scholar
Kazemi, F., & Kiasat, A. R. (2003). Dabco/SOCl2, mild, and convenient reagent for the preparation of symmetrical carboxylic acid anhydrides. Phosphorus, Sulfur, and Silicon and the Related Elements, 178, 2287-2291. DOI: 10.1080/713744563.10.1080/713744563Search in Google Scholar
Kazemi, F., Sharghi, H., & Naseri, M. A. (2004). A cheap, simple and efficient method for the preparation of symmetrical carboxylic acid anhydrides. Synthesis, 2, 205-207. DOI: 10.1055/s-2003-44381.10.1055/s-2003-44381Search in Google Scholar
Kazemi, F., Kiasat, A. R., & Mombaini, B. (2007). Simple preparation of symmetrical carboxylic acid anhydrides by means of Na2CO3/SOCl2. Synthetic Communications, 37, 3219-3223. DOI: 10.1080/00397910701547904.10.1080/00397910701547904Search in Google Scholar
Keshavamurthy, K. S., Vankar, Y. D., & Dhar, D. N. (1982). Preparation of acid anhydrides, amides, and esters using chlorosulfonyl isocyanate as a dehydrating agent. Synthesis, 1982, 506-508. DOI: 10.1055/s-1982-29859.10.1055/s-1982-29859Search in Google Scholar
Kiani, A., Akhlaghinia, B., Rouhi-Saadabad, H., & Bakavoli, M. (2014). Direct synthesis of sulfonyl azides from sulfonic acids. Journal of Sulfur Chemistry, 35, 119-127. DOI: 10.1080/17415993.2013.801476.10.1080/17415993.2013.801476Search in Google Scholar
Kim, J. G., & Jang, D. O. (2001). A convenient method for synthesis of symmetrical acid anhydrides from carboxylic acids with trichloroacetonitrile and triphenylphosphine. Synthetic Communications, 31, 395-399. DOI: 10.1081/scc-100000529. 10.1081/SCC-100000529Search in Google Scholar
Kim, J. J., Park, Y. D., Lee, W. S., Cho, S. D., & Yoon, Y. J. (2003). Facile synthesis of carboxylic anhydrides using 4,5-dichloro-2-[(4-nitrophenyl)sulfonyl]pyridazin-3(2H)- one. Synthesis, 10, 1517-1520. DOI: 10.1055/s-2003-40512.10.1055/s-2003-40512Search in Google Scholar
Kim, J. G., & Jang, D. O. (2009). Synthesis of symmetrical carboxylic acid anhydrides from acyl chlorides in the presence of in metal and DMF. Bulletin of the Korean Chemical Society, 30, 27-28. DOI: 10.5012/bkcs.2009.30.1.027.10.5012/bkcs.2009.30.1.027Search in Google Scholar
Kimura, Y., Matsuura, D., Hanawa, T., & Kobayashi, Y. (2012). New preparation method for Vilsmeier reagent and related imidoyl chlorides. Tetrahedron Letters, 53, 1116-1118. DOI: 10.1016/j.tetlet.2011.12.087.10.1016/j.tetlet.2011.12.087Search in Google Scholar
Kita, Y., Akai, S., Yoshigi, M., Nakajima, Y., Yasuda, H., & Tamura, Y. (1984). A mild and facile synthesis of carboxylic anhydrides. Tetrahedron Letters, 25, 6027-6030. DOI: 10.1016/s0040-4039(01)81751-2.10.1016/S0040-4039(01)81751-2Search in Google Scholar
Kita, Y., Akai, S., Ajimura, N., Yoshigi, M., Tsugoshi, T., Yasuda, H., & Tamura, Y. (1986). Facile and efficient syntheses of carboxylic anhydrides and amides using (trimethylsilyl) ethoxyacetylene. Journal of Organic Chemistry, 51, 4150-5158. DOI: 10.1021/jo00372a010.10.1021/jo00372a010Search in Google Scholar
Kocz, R., Roestamadi, J., & Mobashery, S. (1994). A convenient triphosgene-mediated synthesis of symmetric carboxylic acid anhydrides. Journal of Organic Chemistry, 59, 2913-2914. DOI: 10.1021/jo00089a046.10.1021/jo00089a046Search in Google Scholar
Liesen, G. P., & Sukenik, C. N. (1987). Activated anhydrides of tartaric and malic acids. Journal of Organic Chemistry, 52, 455-457. DOI: 10.1021/jo00379a030.10.1021/jo00379a030Search in Google Scholar
Mariella, R. P., & Brown, K. H. (1971). A novel SN1 displacement: The reaction of tertiary amines with acetic anhydride. Canadian Journal of Chemistry, 49, 3348-3351. DOI: 10.1139/v71-557.10.1139/v71-557Search in Google Scholar
Meienhofer, J., & Gross, E. (1979). The peptides: Analysis, synthesis and biology.Waltham, MA, USA: Academic Press.Search in Google Scholar
Mestres, R., & Palomo, C. (1981). Phosphorus in organic chemistry; I. Mild and convenient reagents for the preparation of symmetrical carboxylic acid anhydrides. Synthesis, 1981, 218-220. DOI: 10.1055/s-1981-29391.Search in Google Scholar
Newman, M. S., & Louge, M. W. (1971). Synthesis of 6,6_- diethynyldiphenic anhydride. Journal of Organic Chemistry, 36, 1398-1401. DOI: 10.1021/jo00809a018.10.1021/jo00809a018Search in Google Scholar
Ogliaruso, M. A., & Wolfe, J. F. (1991). Synthesis of carboxylic acids, esters and their derivatives. New York, NY, USA: Wiley.10.1002/9780470772423Search in Google Scholar
Park, Y. D., Kim, J. J., Kim, H. K., Cho, S. D., Kang, Y. J., Park, K. H., Lee, S. G., & Yoon, Y. J. (2005). ZnCl2-mediated synthesis of carboxylic anhydrides using 2- acyl-4,5-dichloropyridazin-3(2H)-ones. Synthetic Communications, 35, 371-378. DOI: 10.1081/scc-200048939.10.1081/SCC-200048939Search in Google Scholar
Rambacher, P., & Mäke, S. (1968). Simplified process for preparation of anhydrides of aromatic acids. Angewandte Chemie International Edition, 7, 465. DOI: 10.1002/anie.196804651.10.1002/anie.196804651Search in Google Scholar
Rammler, D. H., & Khorana, H. G. (1963). Studies on polynucleotides. XX.1 Amino acid acceptor ribonucleic acids (1). The synthesis and properties of 2__ (or 3__)-O-(DLphenylalanyl)- adenosine, 2__ (or 3__)-O-(DL-phenylalanyl)- uridine and related compounds. Journal of the American Chemical Society, 85, 1997-2002. DOI: 10.1021/ja00896a020.10.1021/ja00896a020Search in Google Scholar
Rinderknecht, H., & Ma, V. (1964). Eine einfache neue Synthese f¨ur Säureanhydride. Helvetica Chimica Acta, 47, 162-165. DOI: 10.1002/hlca.19640470121. (in German) Rinderknecht, H., & Guteinstein, M. (1967). Nicotinic anhydride. Organic Syntheses, 47, 89. DOI: 10.15227/orgsyn.047.0089.10.15227/orgsyn.047.0089Search in Google Scholar
Roof, A. A. M., van-Woerden, H. F., & Cerfontain, H. (1976). The photochemistry of α-aryl carboxylic anhydrides-II: Photolysis of some substituted phenylacetic anhydrides Tetrahedron, 32, 2967-2971. DOI: 10.1016/0040-4020(76) 80154-8.Search in Google Scholar
Rosowsky, A., Bader, H., Cucchi, C. A., Moran, R. G., Kohler, W., & Freisheim, J. H. (1988). Methotrexate analogs. 33. N.delta.-acyl-N.alpha.-(4-amino-4-deoxypteroyl)-L-ornithine derivatives. Synthesis and in vitro antitumor activity. Journal of Medicinal Chemistry, 31, 1332-1337. DOI: 10.1021/ jm00402a013.10.1021/jm00402a013Search in Google Scholar
Rouhi-Saadabad, H., & Akhlaghinia, B. (2014). Direct, rapid and convenient synthesis of esters and thioesters using PPh3/N-chlorobenzotriazole system. Journal of the Brazilian Chemical Society, 25, 253-263. DOI: 10.5935/0103-5053.20130291.10.5935/0103-5053.20130291Search in Google Scholar
Sandler, S. R., & Karo, W. (1972). Organic functional group preparations. Waltham, MA, USA: Academic Press.Search in Google Scholar
Serieys, A., Botuha, C., Chemla, F., Ferreira, F., & Pérez-Luna, A. (2008). Zinc(0)/dimethylformamide-mediated synthesis of symmetrical carboxylic anhydrides from acid chlorides. Tetrahedron Letters, 49, 5322-5323. DOI: 10.1016/j.tetlet. 2008.06.073.Search in Google Scholar
Shambhu, M. B., & Digenis, G. A. (1974). Insoluble resins with mixed carbonic-carboxylic anhydride functions. Preparation and applications as mild selective acylating reagents. Journal of the Chemical Society, Chemical Communications, 1974, 619-620. DOI: 10.1039/c39740000619.10.1039/c39740000619Search in Google Scholar
Sonntag, N. O. V., Trowbridge, J. R., & Krems, I. J. (1954). Reactions of fatty acid chlorides. I. Preparation of fatty acid anhydrides. Journal of the American Oil Chemists’ Society, 31, 151-157. DOI: 10.1007/bf02545703.10.1007/BF02545703Search in Google Scholar
Sugimoto, O., & Tanji, K. I. (2005). An improved method for chlorination of nitrogen-containing π-deficient heteroaromatics using triphenylphosphine and trichloroisocyanuric acid. Heterocycles, 65, 181-185. DOI: 10.3987/com-04-10245.10.3987/COM-04-10245Search in Google Scholar
Sugimoto, O., Harada, Y., & Tanji, K. I. (2012). Phosphonium chloride as a non-volatile chlorinating reagent: preparation and reaction in no solvent or ionic liquid. Heterocycles, 86, 1583-1590. DOI: 10.3987/com-12-s(n)105.10.3987/COM-12-S(N)105Search in Google Scholar
Tachibana, Y., Kawasaki, H., Kihara, N., & Takata, T. (2006). Sequential O- and N-acylation protocol for high-yield preparation and modification of rotaxanes: Synthesis, functionalization, structure, and intercomponent interaction of rotaxanes. Journal of Organic Chemistry, 71, 5093-5104. DOI: 10.1021/jo0601563.10.1021/jo0601563Search in Google Scholar PubMed
Tamura, Y., Kirihara, M., Sasho, M., Akai, S., Sekihachi, J., Okunaka, R., & Kita, Y. (1987a). Total synthesis of a Dring indole analogue of daunomycin. Journal of the Chemical Society, Chemical Communications, 1987, 1474-1476. DOI: 10.1039/c39870001474.10.1039/c39870001474Search in Google Scholar
Tamura, Y., Kirihara, M., Sekihachi, J. I., Okunaka, R., Mohri, S. I., Tsugoshi, T., Akai, S., Sasho, M., & Kita, Y. (1987b). A new synthetic strategy for heteroanthracyclines: Total synthesis of D-ring thiophene analogs of daunomycin. Tetrahedron Letters, 28, 3971-3974. DOI: 10.1016/s0040-4039(00)96434-7.10.1016/S0040-4039(00)96434-7Search in Google Scholar
Tarbel, D. S. (1969). Carboxylic carbonic anhydrides and related compounds. Accounts of Chemical Research, 2, 296-300. DOI: 10.1021/ar50022a002.10.1021/ar50022a002Search in Google Scholar
Wallace, J. M., Jr., & Copenhaver, J. E. (1941). Anhydrides of the normal aliphatic saturated monobasic acids. Journal of the American Chemical Society, 63, 699-700. DOI: 10.1021/ja01848a017. 10.1021/ja01848a017Search in Google Scholar
© 2015 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- One-step preparation of porous copper nanowires electrode for highly sensitive and stable amperometric detection of glyphosate
- Classification of wine distillates using multivariate statistical methods based on their direct GC-MS analysis
- Determination of cigarette papers moisture content by gas chromatography
- Flavonoids inhibiting glycation of bovine serum albumin: affinity–activity relationship
- 10.1515/chempap-2015-0049
- Physicochemical aspects of Trichosporon cutaneum CCY 30-5-10 adhesion and biofilm formation potential on cellophane
- 10.1515/chempap-2015-0031
- 10.1515/chempap-2015-0034
- Preparation of quaternary pyridinium salts as possible proton conductors
- Stable UV absorption material synthesized by intercalation of squaric acid anion into layered double hydroxides
- Electrolytic preparation of nanosized Cu/Ni–Cu multilayered coatings
- Efficient solvent-free synthesis of bis(indolyl)methanes on SiO2 solid support under microwave irradiation
- Facile and direct synthesis of symmetrical acid anhydrides using a newly prepared powerful and efficient mixed reagent
- Practical synthesis of 2,3-dimethoxy-5-hydroxymethyl-6-methyl-1,4-benzoquinone
- 10.1515/chempap-2015-0047
Articles in the same Issue
- One-step preparation of porous copper nanowires electrode for highly sensitive and stable amperometric detection of glyphosate
- Classification of wine distillates using multivariate statistical methods based on their direct GC-MS analysis
- Determination of cigarette papers moisture content by gas chromatography
- Flavonoids inhibiting glycation of bovine serum albumin: affinity–activity relationship
- 10.1515/chempap-2015-0049
- Physicochemical aspects of Trichosporon cutaneum CCY 30-5-10 adhesion and biofilm formation potential on cellophane
- 10.1515/chempap-2015-0031
- 10.1515/chempap-2015-0034
- Preparation of quaternary pyridinium salts as possible proton conductors
- Stable UV absorption material synthesized by intercalation of squaric acid anion into layered double hydroxides
- Electrolytic preparation of nanosized Cu/Ni–Cu multilayered coatings
- Efficient solvent-free synthesis of bis(indolyl)methanes on SiO2 solid support under microwave irradiation
- Facile and direct synthesis of symmetrical acid anhydrides using a newly prepared powerful and efficient mixed reagent
- Practical synthesis of 2,3-dimethoxy-5-hydroxymethyl-6-methyl-1,4-benzoquinone
- 10.1515/chempap-2015-0047