Towards a rationalisation of regioselectivity patterns in reactions of 2-(halogenomethyl)-2-alkenoic esters with carbon nucleophiles

Tetrahedron

Volumn 54, Issue 43, 1998, Pages 13253-13256

  Kaye, Perry T ^a   Robinson, Ross S ^a  

^a RHODES UNIVERSITY   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0032558667     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00811-4     Document Type: Article

References (8)

1. 1. Ameer, F.; Drewes, S.E.; Emslie, N.D.; Kaye, P.T.; Mann, R.L. J. Chem. Soc., Perkin Trans. 1, 1983, 2293-2295.
2. 2. Ameer, F.; Drewes, S.E.; Houston-McMillan, M.S.; Kaye, P.T. J. Chem. Soc., Perkin Trans. 1, 1985, 1143-1145.
3. 3. Ameer, F.; Drewes, S.E.; Houston-McMillan, M.S.; Kaye, P.T. S. Afr. J. Chem., 1986, 39, 57-63.
4. 4. Eagen, M.C.; Cromwell, N.H. J. Org. Chem., 1974, 39, 3863-3866.
5. 5. Magid, R.M. Tetrahedron, 1980, 36, 1901-1930.
6. 1H NMR spectroscopy, but the relative insensitivity of the technique precludes excessive dilution. It was found, however, that at concentrations of ca. 0.02M the reactions could be conveniently followed.
7. 7. See March, J. Advanced Organic Chemistry : Reactions, Mechanisms and Structure, 4th Edn., Wiley, New York, 1992, p. 999.
8. N2') mechanisms would, of course, exhibit first-or second-order kinetic behaviour, respectively. However, given the observed complexity of the kinetic data, their implication as minor, competing pathways is not precluded.