Details

Autor(en) / Beteiligte

• Still, Ian W. J
• Thomas, M. Thomas
• Clish, Alan M

Titel

The Behavior of Thiochromanone and Isothiochromanone Sulfoxides in the Schmidt Reaction: Isolation of a Novel Azide Product from Thiochromone Sulfone

Ist Teil von

• Canadian journal of chemistry, 1975-01, Vol.53 (2), p.276-282

Ort / Verlag

Ottawa, Canada: NRC Research Press

Erscheinungsjahr

1975

Link zum Volltext

Quelle

EZB Electronic Journals Library

Beschreibungen/Notizen

• The Schmidt reaction has been carried out on thiochroman-4-one 1-oxide and a number of related sulfoxides. In all cases lactam formation by attack of HN 3 on the carbonyl group of the keto sulfoxide appears to predominate, with no evidence for sulfoximine formation. The question of aryl vs. alkyl migration, as in other systems, is dependent on the degree of substitution of the alkyl group. When the Schmidt reaction was carried out upon thiochromone 1,1-dioxide two products, the lactam resulting from preferential vinyl migration and a novel α-azido sulfone resulting from 1,4-addition, were obtained.