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Volumn 73, Issue 11, 2008, Pages 4283-4286

Synthesis of stable derivatives of cycloprop-2-ene carboxylic acid

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ADDITION REACTIONS; CARBOXYLIC ACIDS; CHEMICAL REACTIONS; COMPLEXATION; FARM BUILDINGS; LIGHTING; MICROFLUIDICS; ORGANIC ACIDS; PROPYLENE; TELLURIUM COMPOUNDS;

EID: 44949252172     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800042w     Document Type: Article
Times cited : (27)

References (38)
  • 1
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    • 4th ed, de Meijere, A, Ed, Georg Thieme Verlag: Stuttgart
    • (a) Baird, M. S. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 1996; Vol. E17d, pp 2695-2744.
    • (1996) Carbocyclic Three-Membered Ring Compounds , vol.E17d , pp. 2695-2744
    • Baird, M.S.1
  • 4
    • 34547444477 scopus 로고    scopus 로고
    • Selected reviews to the reaction chemistry of cyclopropenes: (a) Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117.
    • Selected reviews to the reaction chemistry of cyclopropenes: (a) Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117.
  • 12
    • 0000897207 scopus 로고
    • For preparations of alkyl cycloprop-2-ene carboxylates: a
    • For preparations of alkyl cycloprop-2-ene carboxylates: (a) Baldwin, J. E.; Villarica, K. A. J. Org. Chem. 1995, 60, 186.
    • (1995) J. Org. Chem , vol.60 , pp. 186
    • Baldwin, J.E.1    Villarica, K.A.2
  • 19
    • 44949264337 scopus 로고    scopus 로고
    • Searle, N. E. In Organic Syntheses; Wiley & Sons; New York, 1963; Collect. IV, pp 424-426.
    • Searle, N. E. In Organic Syntheses; Wiley & Sons; New York, 1963; Collect. Vol. IV, pp 424-426.
  • 22
    • 84981962800 scopus 로고    scopus 로고
    • For syntheses of 2-silyl derivatives of cycloprop-2-ene carboxylic acid, see also: (b) Maier, G.; Hoppe, M.; Reisenauer, H. P.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1982, 21, 437.
    • For syntheses of 2-silyl derivatives of cycloprop-2-ene carboxylic acid, see also: (b) Maier, G.; Hoppe, M.; Reisenauer, H. P.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1982, 21, 437.
  • 26
    • 44949247698 scopus 로고    scopus 로고
    • Compound 3 was also prepared in similar yield with the modification that pivaloyl chloride was used in place of 1-adamantoyl chloride.
    • Compound 3 was also prepared in similar yield with the modification that pivaloyl chloride was used in place of 1-adamantoyl chloride.
  • 27
    • 84987014061 scopus 로고    scopus 로고
    • For reviews on Diels-Alder reactions of cyclopropenes, see ref 2b-d. For Diels-Alder reactions of cycloprop-2-ene carboxylates, see ref 3b and: (a) Paulini, K, Reissig, H. U. J. Prakt. Chem. Chem. Z. 1995, 337, 55
    • For reviews on Diels-Alder reactions of cyclopropenes, see ref 2b-d. For Diels-Alder reactions of cycloprop-2-ene carboxylates, see ref 3b and: (a) Paulini, K.; Reissig, H. U. J. Prakt. Chem. Chem. Z. 1995, 337, 55.
  • 32
    • 0346502724 scopus 로고    scopus 로고
    • For other, recent examples of Diels-Alder reactions of cyclopropenes, see: f
    • For other, recent examples of Diels-Alder reactions of cyclopropenes, see: (f) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406.
    • (2004) J. Org. Chem , vol.69 , pp. 406
    • Orugunty, R.S.1    Wright, D.L.2    Battiste, M.A.3    Helmich, R.J.4    Abboud, K.5
  • 34
    • 0034818567 scopus 로고    scopus 로고
    • For recent theoretical studies on the endo selectivity of cyclopropene Diels-Alder reactions, see: a
    • For recent theoretical studies on the endo selectivity of cyclopropene Diels-Alder reactions, see: (a) Xidos, J. D.; Gosse, T. L.; Burke, E. D.; Poirer, R. A.; Burnell, D. J. J. Am. Chem. Soc. 2001, 123, 5482.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 5482
    • Xidos, J.D.1    Gosse, T.L.2    Burke, E.D.3    Poirer, R.A.4    Burnell, D.J.5
  • 38
    • 44949089930 scopus 로고    scopus 로고
    • For the preparations of 2-4, similar yields were obtained when 5 was added as neat material or as a ∼30% wt solution in MTBE.
    • For the preparations of 2-4, similar yields were obtained when 5 was added as neat material or as a ∼30% wt solution in MTBE.


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