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Volumn , Issue 2, 1999, Pages 409-417

Deprotonation of oxazolinyloxiranes: Formation of substituted acyloxiranes

Author keywords

Acyloxiranes; Deprotonation; Oxazolidines; Oxazolinyloxiranyllithium compounds; Oxiranyloxazolines

Indexed keywords

ETHYLENE OXIDE DERIVATIVE;

EID: 0032838844     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199902)1999:2<409::aid-ejoc409>3.0.co;2-z     Document Type: Article
Times cited : (24)

References (53)
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    • For a review on oxiranyl anions see: T. Satoh, Chem. Rev. 1996, 96, 3303-3325.
    • (1996) Chem. Rev. , vol.96 , pp. 3303-3325
    • Satoh, T.1
  • 28
    • 0001117008 scopus 로고
    • and references therein
    • [16d] J. K. Crandall, M. Apparu, Org. React. 1983, 29, 345-443 and references therein.
    • (1983) Org. React. , vol.29 , pp. 345-443
    • Crandall, J.K.1    Apparu, M.2
  • 35
    • 0001285095 scopus 로고
    • That an epoxy group, through the nonbonding electrons of the oxygen atom, is a good effective acceptor of hydrogen bonds, is well known; see: C. R. Johnson, C. J. Cheer, J. Am. Chem. Soc. 1968, 90, 178-183.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 178-183
    • Johnson, C.R.1    Cheer, C.J.2
  • 37
    • 0344361941 scopus 로고
    • All of the structures were optimized with no symmetry constraints, unless otherwise stated, and using the keyword PRECISE in order to meet rigorous criteria. In order to ensure that results did not involve an artifact, we used different geometries as starting structures in which all of the feasible conformations were considered (i.e. presence or absence of hydrogen bonding to the epoxy oxygen or oxazolinyl heteroatoms, steric hindrance). MOPAC 6.0: J. J. P. Stewart, QCPE 455, 1990. All of the calculations were performed using the keywords PM3, EF, and PRECISE.
    • (1990) QCPE , vol.455
    • Stewart, J.J.P.1
  • 41
    • 0001310099 scopus 로고
    • Signals of carbon atoms that are sterically perturbed appear at higher field than those of similar carbon atoms that are not sterically crowded, as reported; D. M. Grant, B. V. Cheney, J. Am. Chem. Soc. 1967, 89, 5315-5318.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 5315-5318
    • Grant, D.M.1    Cheney, B.V.2
  • 44
    • 0345224669 scopus 로고    scopus 로고
    • note
    • [25c] The syn (6) and anti (7) structures of the two diastereomeric chlorohydrins were determined by the ratios and structures of the (E)-(1j) and (Z)-oxazolinyl epoxides (1m), respectively.
  • 46
    • 0027172512 scopus 로고
    • [26b] Ethynyl-stabilized oxiranyl anions from optically pure cis-disubstituted ethynyloxiranes were also proved to be configurationally stable: D. Grandjean, P. Pale, J. Chuche, Tetrahedron: Asymmetry 1993, 4, 1991-1994.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1991-1994
    • Grandjean, D.1    Pale, P.2    Chuche, J.3
  • 51
    • 0001497764 scopus 로고
    • The formylation of a Grignard reagent via 4,4-dimethyl-2-oxazoline was performed by A. I. Meyers et al. by adding a Grignard reagent containing 2.0 equiv. of hexamethylphosphoramide (HMPA) to a THF suspension of the corresponding oxazolinium salt. In this case aliphatic Grignard reagents were not successfully formylated: A. I. Meyers, E. W. Collington, J. Am. Chem. Soc. 1970, 92, 6676-6678.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 6676-6678
    • Meyers, A.I.1    Collington, E.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.