REMOTE EPSILON-SECONDARY ISOTOPE EFFECT IN THE REACTION OF TETRACYANOETHYLENE WITH 2,5-DIMETHYL-2,4-HEXADIENE - A STEP-WISE MECHANISM

Authors
VASSILIKOGIANNAKIS G ORFANOPOULOS M
Citation
G. Vassilikogiannakis et M. Orfanopoulos, REMOTE EPSILON-SECONDARY ISOTOPE EFFECT IN THE REACTION OF TETRACYANOETHYLENE WITH 2,5-DIMETHYL-2,4-HEXADIENE - A STEP-WISE MECHANISM, Tetrahedron letters, 37(17), 1996, pp. 3075-3078
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
17
Year of publication
1996
Pages
3075 - 3078
Database
ISI
SICI code
0040-4039(1996)37:17<3075:REIEIT>2.0.ZU;2-0
Abstract
Cycloaddition of TCNE to hyl-1',1',1'-d(3)-5-methy-2,4-hexadiene-1,1,1 -d(3) (DMHD-d(6)) shows a substantial secondary isotope effect, which depends on solvent polarity. This remote epsilon-secondary isotope eff ect is a result of hyperconjugation in the dipolar intermediate which is formed in the rate determining step. (C) 1996 Elsevier Science Ltd.