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Intramolecular Oxygen Transfer on the Ozonolysis of a Diphenylcyclopentene Derivative
Author(s) -
Jefford Charles W.,
Boukouvalas John,
Jaggi Danielle,
Kohmoto Shigeo,
Bernardinelli GéRald
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690422
Subject(s) - ozonolysis , ozonide , chemistry , yield (engineering) , intramolecular force , substituent , derivative (finance) , acetal , medicinal chemistry , stereochemistry , organic chemistry , materials science , economics , financial economics , metallurgy
The ozonolysis of cis ‐3,4a,7,7a‐tetrahydro‐3,3‐dimethyl‐6,7a‐diphenylcyclopenta[1,2,4]trioxine ( 1 ) in CH 2 Cl 2 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/CH 2 Cl 2 20:3 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.
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