Photochemical reactions. 140 th  Communication . Acid‐catalyzed rearrangement and electron transfer photooxygenation of cyclopropanols and their silyl ethers | Zendy

Scheller Markus E. | Zendy; Mathies Peter | Zendy; Petter Walter | Zendy; Frei Bruno | Zendy

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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 .

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