Citation
A. Burritt et al., CORNER VERSUS EDGE PROTONATION OF CYCLOPROPANE, Journal of organic chemistry, 60(23), 1995, pp. 7670-7673
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00223263
Volume
60
Issue
23
Year of publication
1995
Pages
7670 - 7673
Database
ISI
SICI code
0022-3263(1995)60:23<7670:CVEPOC>2.0.ZU;2-A
Abstract
Acid-catalyzed addition of methanol to 1 occurs by rupture of the inte
rnal carbon-carbon bond of the cyclopropane to give 2 with both retent
ion and inversion at the site of electrophilic attack (4:5, 1.3:1.0).
Nucleophilic attack occurs with inversion without relaxation of the co
rner- and edge-protonated cyclopropanes to a secondary cation.