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Photochemical reactions. 140 th Communication . Acid‐catalyzed rearrangement and electron transfer photooxygenation of cyclopropanols and their silyl ethers
Author(s) -
Scheller Markus E.,
Mathies Peter,
Petter Walter,
Frei Bruno
Publication year - 1984
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.19840670712
Subject(s) - photooxygenation , chemistry , silylation , ether , photochemistry , catalysis , hydrolysis , electron transfer , silyl ether , medicinal chemistry , singlet oxygen , organic chemistry , oxygen
On acid‐catalyzed hydrolysis, the tricyclic compounds 2 and 10 , incorporating cyclopropyl‐silyl‐ether moieties undergo rearrangement to the cis ‐decalones 3 and 7 , respectively. Hydrolysis of 2 and 10 in the presence of oxygen leads additionally to the formation of the 1,2‐dioxolan‐3‐ols 9 and 13 , respectively, which involves an electron‐transfer oxygenation process as could be demonstrated by photooxygenation of the silyl ether 10 and the cyclopropanol 14 in the presence of 9,10‐dicyanoanthracene. The configurations of 3 and 9 were assigned by X‐ray analysis of the latter compound as well as of the p ‐nitrobenzoate 8 of 3 .