Scientific article
English

Intramolecular Oxygen Transfer on the Ozonolysis of a Diphenylcyclopentene Derivative

Published inHelvetica chimica acta, vol. 69, no. 4, p. 941-948
Publication date1986-06-18
Abstract

The ozonolysis of cis-3,4a,7,7a-tetrahydro-3,3-dimethyl-6,7a-diphenylcyclopenta[1,2,4]trioxine (1) in CH2Cl2 at −78° gave the secondary endo ozonide 2 (43% yield) and an acetal 3 (27% yield) derived from O-insertion at the ortho position of the C(7a) phenyl substituent. Both structures were elucidated by X-ray. Repetition of the ozonolysis in MeOH/CH2Cl220:3 at −78° also gave the same two products in 12 and 15% yields, repectively, together with the hemiperacetal 4 (54% yield) formally derived from the secondary ozonide by addition of MeOH.

Citation (ISO format)
JEFFORD, Charles et al. Intramolecular Oxygen Transfer on the Ozonolysis of a Diphenylcyclopentene Derivative. In: Helvetica chimica acta, 1986, vol. 69, n° 4, p. 941–948. doi: 10.1002/hlca.19860690422
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Journal ISSN0018-019X
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