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The Reaction of Singlet Oxygen with 1,3‐Dimethylindole in the Presence of Aldehydes. Formation of 1,2,4‐Trioxanes
Author(s) -
Jefford Charles W.,
Jaggi Danielle,
Boukouvalas John,
Kohmoto Shigeo,
Bernardinelli Gérald
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.19840670423
Subject(s) - chemistry , diastereomer , acetaldehyde , peroxide , singlet oxygen , oxygen , singlet state , cis–trans isomerism , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , physics , ethanol , nuclear physics , excited state
The dye‐sensitized photo‐oxygenation of 1,3‐dimethylindole in the presence of aldehydes initially generates a zwitterionic peroxide which condenses with the carbonyl function to give the corresponding cis ‐fused 1,2,4‐trioxanes. Acetaldehyde gives a pair of diastereomers, one of whose structures was determined by X‐ray analysis ( cis , cis isomer), whereas pivaladehyde gives only the cis , cis diastereomer.