Exceptionally Stable Ozonides. Influence of Methyl Substituents on the Course of Cyclopentene Ozonolyses and on the Reactivities of Ozonides
作者:Herbert Mayr、Janusz Baran、Elfriede Will、Hideyuki Yamakoshi、Koichi Teshima、Masatomo Nojima
DOI:10.1021/jo00096a059
日期:1994.8
Ozonolyses of 1,2,3,3,4,4,5,5-octamethyl- (1a), 1,2,3,3,4,4,5-heptamethyl- (1b), and 1,2,3,3,4,4-hexamethyl cyclopentenes (1c) in methanol did not yield the ordinary hemiperacetals but gave the corresponding ozonides 6a-c instead. The ozonides 6a,b were extremely stable nd remained intact even when refluxed with triphenylphosphine in tetrahydrofuran. Cycloreversion of the primary ozonides from unsymmetrically substituted 1,2,3,3-tetramethylcyclopentene (1d) and 1,5,5-trimethylcyclopentene (1g) was highly regioselective to yield the intermediate omega-oxo carbonyl oxides with the geminal methyl groups remote from the carbonyl oxide groups.