THE CLEAVAGE OF AN UNUSUALLY REFRACTIVE EPOXIDE GROUP IN THE DERIVATIVES OF SESQUITERPENE LACTONE ENHYDRIN

Authors
KRISHNASWAMY NR RAMJI N
Citation
Nr. Krishnaswamy et N. Ramji, THE CLEAVAGE OF AN UNUSUALLY REFRACTIVE EPOXIDE GROUP IN THE DERIVATIVES OF SESQUITERPENE LACTONE ENHYDRIN, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 35(6), 1996, pp. 541-545
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry → ACNP
ISSN journal
03764699
Volume
35
Issue
6
Year of publication
1996
Pages
541 - 545
Database
ISI
SICI code
0376-4699(1996)35:6<541:TCOAUR>2.0.ZU;2-O
Abstract
The sesquiterpene lactone enhydrin 1 and its derivatives 2 show extrao rdinary stability of its nuclear epoxide, which is stable under hydrol ytic oxidative and reductive conditions. The unusual stability is attr ibutable to the steric effect in 1 and the transannular hydrogen bondi ng in 2. Cleavage of this epoxide in the diol 2 and its derivatives ha ve been investigated and evidences to explain its unusual stability ha ve been reported.