메뉴 건너뛰기




Volumn 38, Issue 16, 2008, Pages 2845-2856

Cl3CCONH2/PPh3: A versatile reagent for synthesis of esters

Author keywords

Acid chloride; Ester; One pot conversion; PPh3; Trichloroacetamide

Indexed keywords

ACID; ALCOHOL; CARBOXYLIC ACID DERIVATIVE; CHLORIDE; ESTER;

EID: 49949085741     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801979361     Document Type: Article
Times cited : (7)

References (40)
  • 3
  • 4
  • 5
    • 12444283342 scopus 로고
    • A new method of forming peptide bonds
    • Sheehan, J. C.; Hess, G. P. A new method of forming peptide bonds. J. Am. Chem. Soc. 1955, 77, 1067-1068;
    • (1955) J. Am. Chem. Soc , vol.77 , pp. 1067-1068
    • Sheehan, J.C.1    Hess, G.P.2
  • 6
    • 1842442545 scopus 로고
    • Notes-A convenient synthesis of water-soluble carbodiimides
    • (b) Sheehan, J.; Cruickshank, P. A. Notes-A convenient synthesis of water-soluble carbodiimides. J. Org. Chem. 1961, 26, 2525-2528;
    • (1961) J. Org. Chem , vol.26 , pp. 2525-2528
    • Sheehan, J.1    Cruickshank, P.A.2
  • 7
    • 42249094799 scopus 로고
    • Recent developments in the carbodiimide chemistry
    • (c) Mikolajczyk, M.; Kielbasinski, P. Recent developments in the carbodiimide chemistry. Tetrahedron 1981, 37, 233-284;
    • (1981) Tetrahedron , vol.37 , pp. 233-284
    • Mikolajczyk, M.1    Kielbasinski, P.2
  • 8
    • 50549213950 scopus 로고
    • On the mechanism of carboxyl condensations by carbodiimides
    • (d) Doleschall, G.; Lempert, K. On the mechanism of carboxyl condensations by carbodiimides. Tetrahedron Lett. 1963, 4, 1195-1199;
    • (1963) Tetrahedron Lett , vol.4 , pp. 1195-1199
    • Doleschall, G.1    Lempert, K.2
  • 9
    • 22944470620 scopus 로고
    • Carbodiimide chemistry: Recent advances
    • (e) Williams, A.; Ibrahim, I. T. Carbodiimide chemistry: Recent advances. Chem. Rev. 1981, 81, 589-636;
    • (1981) Chem. Rev , vol.81 , pp. 589-636
    • Williams, A.1    Ibrahim, I.T.2
  • 10
    • 33845183983 scopus 로고
    • Solvent dependence of carboxylic acid condensations with dicyclohexylcarbodiimide
    • (f) Balcom, B. J.; Petersen, N. O. Solvent dependence of carboxylic acid condensations with dicyclohexylcarbodiimide. J. Org. Chem. 1989, 54, 1922-1927.
    • (1989) J. Org. Chem , vol.54 , pp. 1922-1927
    • Balcom, B.J.1    Petersen, N.O.2
  • 11
    • 33845375891 scopus 로고
    • (Fluoren-9-ylmethoxy)carbonyl (Fmoc) amino acid chlorides: Synthesis, characterization, and application to the rapid synthesis of short peptide segments
    • Carpino, L. A.; Cohen, B.; Stephens Jr., K. E.; Sadet-Aalaee, S. Y.; Langridge, D. C. (Fluoren-9-ylmethoxy)carbonyl (Fmoc) amino acid chlorides: Synthesis, characterization, and application to the rapid synthesis of short peptide segments. J. Org. Chem. 1986, 51, 3732-3734;
    • (1986) J. Org. Chem , vol.51 , pp. 3732-3734
    • Carpino, L.A.1    Cohen, B.2    Stephens Jr., K.E.3    Sadet-Aalaee, S.Y.4    Langridge, D.C.5
  • 12
    • 0001494124 scopus 로고    scopus 로고
    • Imino Diels-Alder-based construction of a piperidine A-ring unit for total synthesis of the marine hepatotoxin cylindrospermopsin
    • (b) Heintzelman, G. R.; Weinreb, S. M.; Parvez, M. Imino Diels-Alder-based construction of a piperidine A-ring unit for total synthesis of the marine hepatotoxin cylindrospermopsin. J. Org. Chem. 1996, 61, 4594-4599;
    • (1996) J. Org. Chem , vol.61 , pp. 4594-4599
    • Heintzelman, G.R.1    Weinreb, S.M.2    Parvez, M.3
  • 14
    • 0003951441 scopus 로고
    • S. Patai Ed, Interscience: London
    • (d) Antell, M. F. In The Chemistry of Acyl Halides; S. Patai (Ed.); Interscience: London, 1972; pp. 40-44;
    • (1972) The Chemistry of Acyl Halides , pp. 40-44
    • Antell, M.F.1
  • 15
    • 84920358849 scopus 로고    scopus 로고
    • Pearson, A. J.; Roush, W. R. (Eds.). Handbook of Reagents for Organic Synthesis: Activating Agents and Protecting Groups; Wiley: New York, 1999; pp. 333, 335-338, and 370-373.
    • (e) Pearson, A. J.; Roush, W. R. (Eds.). Handbook of Reagents for Organic Synthesis: Activating Agents and Protecting Groups; Wiley: New York, 1999; pp. 333, 335-338, and 370-373.
  • 16
    • 0003922516 scopus 로고    scopus 로고
    • 7th ed, Prentice-Hall International: Englewood Cliffs, N. J
    • Morrison, R. T.; Boyd, R. N. Organic Chemistry, 7th ed.; Prentice-Hall International: Englewood Cliffs, N. J., 1999; pp. 760-762.
    • (1999) Organic Chemistry , pp. 760-762
    • Morrison, R.T.1    Boyd, R.N.2
  • 17
    • 33947336465 scopus 로고
    • Preparation of acid chlorides under very mild conditions
    • (a) Lee, J. B. Preparation of acid chlorides under very mild conditions. J. Am. Chem. Soc. 1966, 88, 3440-3441;
    • (1966) J. Am. Chem. Soc , vol.88 , pp. 3440-3441
    • Lee, J.B.1
  • 18
    • 0001293975 scopus 로고
    • A simple method for the synthesis of amides
    • (b) Barstow, L. E.; Hruby, V. J. A simple method for the synthesis of amides. J. Org. Chem. 1971, 36, 1305-1306;
    • (1971) J. Org. Chem , vol.36 , pp. 1305-1306
    • Barstow, L.E.1    Hruby, V.J.2
  • 19
    • 0000263341 scopus 로고
    • Preparation of alkyl chlorides, acid chlorides, and amides using polymer-supported phosphines and carbon tetrachloride: Mechanism of these reactions
    • (c) Harrison, C. R.; Hodge, P.; Hunt, B. J.; Khoshdel, E.; Richardson, G. Preparation of alkyl chlorides, acid chlorides, and amides using polymer-supported phosphines and carbon tetrachloride: Mechanism of these reactions. J. Org. Chem. 1983, 48, 3721-3728.
    • (1983) J. Org. Chem , vol.48 , pp. 3721-3728
    • Harrison, C.R.1    Hodge, P.2    Hunt, B.J.3    Khoshdel, E.4    Richardson, G.5
  • 20
    • 0000755105 scopus 로고
    • Cyanuric chloride: A useful reagent for converting carboxylic acids into chlorides, esters, amides and peptides
    • Venkataraman, K.; Wagle, D. R. Cyanuric chloride: A useful reagent for converting carboxylic acids into chlorides, esters, amides and peptides. Tetrahedron Lett. 1979, 32, 3037-3040.
    • (1979) Tetrahedron Lett , vol.32 , pp. 3037-3040
    • Venkataraman, K.1    Wagle, D.R.2
  • 22
    • 0030848431 scopus 로고    scopus 로고
    • A rapid, mild, and acid-free procedure for the preparation of acyl chorides including formyl chloride
    • Villeneuve G. B.; Chan, T. H. A rapid, mild, and acid-free procedure for the preparation of acyl chorides including formyl chloride. Tetrahedron Lett. 1997, 38, 6489-6492.
    • (1997) Tetrahedron Lett , vol.38 , pp. 6489-6492
    • Villeneuve, G.B.1    Chan, T.H.2
  • 23
    • 32244442226 scopus 로고    scopus 로고
    • Facile conversion of alcohols into their bromides and iodides by N-bromo and N-iodosaccharins/triphenylphosphine under neutral conditions
    • Firouzabadi, H.; Iranpoor, N.; Ebrahimzadeh, F. Facile conversion of alcohols into their bromides and iodides by N-bromo and N-iodosaccharins/triphenylphosphine under neutral conditions. Tetrahedron Lett. 2006, 47, 1771-1775.
    • (2006) Tetrahedron Lett , vol.47 , pp. 1771-1775
    • Firouzabadi, H.1    Iranpoor, N.2    Ebrahimzadeh, F.3
  • 25
    • 33745608945 scopus 로고    scopus 로고
    • A mild and efficient reaction for conversion of carboxylic acids into acid bromides with ethyl tribromoacetate/triphenylphosphine under acid-free conditions
    • Kang, D. H.; Joo, T. Y.; Lee, E. H.; Chaysripongkul, S.; Chavasiri, W.; Jang, D. O. A mild and efficient reaction for conversion of carboxylic acids into acid bromides with ethyl tribromoacetate/triphenylphosphine under acid-free conditions. Tetrahedron Lett. 2006, 47, 5693-5696.
    • (2006) Tetrahedron Lett , vol.47 , pp. 5693-5696
    • Kang, D.H.1    Joo, T.Y.2    Lee, E.H.3    Chaysripongkul, S.4    Chavasiri, W.5    Jang, D.O.6
  • 26
    • 0033575468 scopus 로고    scopus 로고
    • A mild and efficient procedure for the preparation of acid chlorides from carboxylic acids
    • Jang, D. O.; Park, D. J.; Kim, J. A mild and efficient procedure for the preparation of acid chlorides from carboxylic acids. Tetrahedron Lett. 1999, 40, 5323-5326;
    • (1999) Tetrahedron Lett , vol.40 , pp. 5323-5326
    • Jang, D.O.1    Park, D.J.2    Kim, J.3
  • 27
    • 0041629076 scopus 로고    scopus 로고
    • One-pot preparation of esters from carboxylic acids using the PPh3-CCl3CN system
    • (b) Jang, D. O.; Cho, D. H.; Kim, J.-G. One-pot preparation of esters from carboxylic acids using the PPh3-CCl3CN system. Synth. Commun. 2003, 33, 2885-2890;
    • (2003) Synth. Commun , vol.33 , pp. 2885-2890
    • Jang, D.O.1    Cho, D.H.2    Kim, J.-G.3
  • 28
    • 0035082593 scopus 로고    scopus 로고
    • A convenient method for synthesis of symmetrical acid anhydrides from carboxylic acids with trichloroacetronitrile and triphenylphosphine
    • (c) Kim, J.; Jang, D. O. A convenient method for synthesis of symmetrical acid anhydrides from carboxylic acids with trichloroacetronitrile and triphenylphosphine. Synth. Commun. 2001, 31, 395-399.
    • (2001) Synth. Commun , vol.31 , pp. 395-399
    • Kim, J.1    Jang, D.O.2
  • 30
    • 13544264234 scopus 로고
    • α-Chloro enamines, reactive intermediates for synthesis: 1-Chloro-N, N, 2-trimethylpropenylamine
    • Haveux, B.; Dekoker, A.; Rens, M.; Sidani, A. R.; Toye, J.; Ghosez, L. α-Chloro enamines, reactive intermediates for synthesis: 1-Chloro-N, N, 2-trimethylpropenylamine. Org. Syn. Coll. 1988, 6, 282.
    • (1988) Org. Syn. Coll , vol.6 , pp. 282
    • Haveux, B.1    Dekoker, A.2    Rens, M.3    Sidani, A.R.4    Toye, J.5    Ghosez, L.6
  • 35
    • 24744433107 scopus 로고    scopus 로고
    • Alumina sulfuric acid as a novel heterogeneous system for esterification of carboxylic acids in solvent free conditions
    • Hashem, S.; Sarvari, M. H.; Razieh, E. Alumina sulfuric acid as a novel heterogeneous system for esterification of carboxylic acids in solvent free conditions. J. Chem. Res. 2005, 8, 488-491;
    • (2005) J. Chem. Res , vol.8 , pp. 488-491
    • Hashem, S.1    Sarvari, M.H.2    Razieh, E.3
  • 36
    • 0001435351 scopus 로고
    • A mild and efficient alumina-promoted synthesis of t-butyl esters
    • (b) Nagasawa, K.; Yoshitake, S.; Amiya, T.; Ito, K. A mild and efficient alumina-promoted synthesis of t-butyl esters. Synth. Commun. 1990, 20, 2033-2040.
    • (1990) Synth. Commun , vol.20 , pp. 2033-2040
    • Nagasawa, K.1    Yoshitake, S.2    Amiya, T.3    Ito, K.4
  • 37
    • 0030055809 scopus 로고    scopus 로고
    • Insecticidal constituents from rhizomes of Zingiber cassumunar and Kaempferia rotunda
    • Nugroho, B. W.; Schwarz, B.; Wray, V.; Proksch, P. Insecticidal constituents from rhizomes of Zingiber cassumunar and Kaempferia rotunda. Phytochemistry 1996, 41, 129-132.
    • (1996) Phytochemistry , vol.41 , pp. 129-132
    • Nugroho, B.W.1    Schwarz, B.2    Wray, V.3    Proksch, P.4
  • 38
    • 0035136046 scopus 로고    scopus 로고
    • Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst
    • Weber, N.; Weitekamo, P.; Mukherjee, K. D. Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst. J. Agric. Food Chem. 2001, 49, 67-71.
    • (2001) J. Agric. Food Chem , vol.49 , pp. 67-71
    • Weber, N.1    Weitekamo, P.2    Mukherjee, K.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.