THE ALPHA-SECONDARY ISOTOPE EFFECT IN THE 1,2-SIMILAR-TO-C REARRANGEMENT OF CYCLOPROPYLCHLOROCARBENE

Authors
MOSS RA LIU WG KROGHJESPERSEN K
Citation
Ra. Moss et al., THE ALPHA-SECONDARY ISOTOPE EFFECT IN THE 1,2-SIMILAR-TO-C REARRANGEMENT OF CYCLOPROPYLCHLOROCARBENE, Tetrahedron letters, 34(38), 1993, pp. 6025-6028
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
38
Year of publication
1993
Pages
6025 - 6028
Database
ISI
SICI code
0040-4039(1993)34:38<6025:TAIEIT>2.0.ZU;2-N
Abstract
The experimetal alpha-secondary kinetic isotope effect for the rearran gement of (2,2-dideuteriocyclopropyl)chlorocarbene, 2-d2, to chlorocyc lobutenes, 4 and 5, is k(H)/k(D) = 1.20 at 21-degrees-C. The correspon ding value calculated by ab initio electronic structure methods is 1.1 2. The isotope effect very largely originates in hybridization changes at the migrating carbon atom.