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Interception of an Intermediate Thiocarbonyl Ylide by NH-Compounds


Mloston, Grzegorz; Janicka, Ewa; Woznicka, Marta; Linden, Anthony; Heimgartner, Heinz (2003). Interception of an Intermediate Thiocarbonyl Ylide by NH-Compounds. Polish Journal of Chemistry, 77:1805-1817.

Abstract

By thermal decomposition of 1,1,3,3-tetramethyl-5-thia-7,8-diazaspiro[3.4]octan-2-one (1), 2,2,4,4-tetramethyl-3-thioxocyclobutanone S-methylide (2) was generated as an intermediate. This reactive 'thiocarbonyl ylide‘ was trapped by protic agents such as alcohols, NH- and SH-acidic compounds to give 1,3-adducts of the acetal type. In a mixture of methanol and ammonia, the spiroheterocycle 1 was deprotonated and competitive ring opening of the 2,5-dihydro-1,3,4-thiadiazole and the cyclobutane ring occurred to give the hydrazono derivative 7 and the 1,3,4-thiadiazole 8, respectively. Surprisingly, 2 was intercepted by maleimide in a 1,3-dipolar cycloaddition.

Abstract

By thermal decomposition of 1,1,3,3-tetramethyl-5-thia-7,8-diazaspiro[3.4]octan-2-one (1), 2,2,4,4-tetramethyl-3-thioxocyclobutanone S-methylide (2) was generated as an intermediate. This reactive 'thiocarbonyl ylide‘ was trapped by protic agents such as alcohols, NH- and SH-acidic compounds to give 1,3-adducts of the acetal type. In a mixture of methanol and ammonia, the spiroheterocycle 1 was deprotonated and competitive ring opening of the 2,5-dihydro-1,3,4-thiadiazole and the cyclobutane ring occurred to give the hydrazono derivative 7 and the 1,3,4-thiadiazole 8, respectively. Surprisingly, 2 was intercepted by maleimide in a 1,3-dipolar cycloaddition.

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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:2003
Deposited On:09 Oct 2013 13:52
Last Modified:05 Apr 2016 17:02
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Polish State Committee for Scientific Research, F. Hoffmann-La Roche AG, Basel

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