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Reactions of alpha-diazocycloalkanones with thiocarbonyl compounds


Kelmendi, Bashkim; Mloston, Grzegorz; Heimgartner, Heinz (2000). Reactions of alpha-diazocycloalkanones with thiocarbonyl compounds. Heterocycles, 52:475-482.

Abstract

Reactions of 2-diazocyclohexanone (7) with thioketones and a 1,3-thiazole-5(4H)-thione in THF at 50-60°C in the presence of 10% LiClO4 proceeded by elimination of N2 and yielded 4,5,6,7-tetrahydro-1,3-benzoxathiole derivatives (13-17). In the case of 2,2,4,4-tetramethylcyclobutane-1,3-dithione (12), a 1:5 mixture of cis- and trans-bisadducts (cis/trans-17) was obtained. Under analogous conditions, no reactions occurred with 5,5-dimethyl-2-diazocyclohexane-1,3-dione (18). Only in the presence of 2% Rh2(OAc)4, 18 reacted with dithione (12) yielding the 1,3-benzoxathiole derivative (19).

Abstract

Reactions of 2-diazocyclohexanone (7) with thioketones and a 1,3-thiazole-5(4H)-thione in THF at 50-60°C in the presence of 10% LiClO4 proceeded by elimination of N2 and yielded 4,5,6,7-tetrahydro-1,3-benzoxathiole derivatives (13-17). In the case of 2,2,4,4-tetramethylcyclobutane-1,3-dithione (12), a 1:5 mixture of cis- and trans-bisadducts (cis/trans-17) was obtained. Under analogous conditions, no reactions occurred with 5,5-dimethyl-2-diazocyclohexane-1,3-dione (18). Only in the presence of 2% Rh2(OAc)4, 18 reacted with dithione (12) yielding the 1,3-benzoxathiole derivative (19).

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2000
Deposited On:29 Oct 2013 10:59
Last Modified:05 Apr 2016 17:05
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel

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