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Cascade reaction in a three-component system including adamantanethione, phenyl azide, and dimethyl fumarate


Mloston, Grzegorz; Romanski, Jaroslaw; Linden, Anthony; Heimgartner, Heinz (1996). Cascade reaction in a three-component system including adamantanethione, phenyl azide, and dimethyl fumarate. Polish Journal of Chemistry, 70:595-602.

Abstract

The major product of the three-component reaction with adamantanethione (1), dimethyl fumarate (6), and phenyl azide at 80°C has been determined as the 1-azabuta-1,3-diene derivative 7 by X-ray crystallography. A similar amount of the symmetric dispiro-1,2,4-trithiolane 8 was also found in the reaction mixture. The reaction with N-phenyl maleimide instead of the fumarate, yielded the known 4,5-dihydro-1,2,3-triazole derivative 9, and the three-component system with 1,3-thiazole-5(4H)-thione 10, dimethyl fumarate (6), and phenyl azide gave a mixture of imine 11, 4,5-dihydro-1,2,3-triazole-4,5-dicarboxylate 12 and the diazo compound 13. A mechanism via a cascade of reactions is proposed to rationalize the formation of 7.

Abstract

The major product of the three-component reaction with adamantanethione (1), dimethyl fumarate (6), and phenyl azide at 80°C has been determined as the 1-azabuta-1,3-diene derivative 7 by X-ray crystallography. A similar amount of the symmetric dispiro-1,2,4-trithiolane 8 was also found in the reaction mixture. The reaction with N-phenyl maleimide instead of the fumarate, yielded the known 4,5-dihydro-1,2,3-triazole derivative 9, and the three-component system with 1,3-thiazole-5(4H)-thione 10, dimethyl fumarate (6), and phenyl azide gave a mixture of imine 11, 4,5-dihydro-1,2,3-triazole-4,5-dicarboxylate 12 and the diazo compound 13. A mechanism via a cascade of reactions is proposed to rationalize the formation of 7.

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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:1996
Deposited On:25 Nov 2013 08:08
Last Modified:18 Apr 2018 11:44
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Polish State Committee for Scientific Research (Grant No. 3 TO9A 157 10), Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
OA Status:Closed
Related URLs:http://www.ichf.edu.pl/pjch/
Project Information:
  • : Funder
  • : Grant ID
  • : Project TitlePolish State Committee for Scientific Research (Grant No. 3 TO9A 157 10)
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSwiss National Science Foundation
  • : Funder
  • : Grant ID
  • : Project TitleF. Hoffmann-La Roche AG, Basel

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