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Chemo- and stereoselectivity in 1,3-dipolar cycloadditions of thiocarbonyl ylides with a 1,4-methanonaphthalene-5,8-dione derivative


Mloston, Grzegorz; Celeda, Malgorzata; Heimgartner, Heinz (2003). Chemo- and stereoselectivity in 1,3-dipolar cycloadditions of thiocarbonyl ylides with a 1,4-methanonaphthalene-5,8-dione derivative. Heterocycles, 59(2):767-777.

Abstract

The reaction of 1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione (2) with aliphatic and aromatic thiocarbonyl ylides (1a-c) gave polycyclic tetrahydrothiophene derivatives (5a-c) by a chemo- and stereoselective 1,3-dipolar cycloaddition. The 1,3-dipoles (1a-c) were generated by thermal elimination of nitrogen from the corresponding 2,5-dihydro-1,3,4-thiadiazoles (4a-c).

Abstract

The reaction of 1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione (2) with aliphatic and aromatic thiocarbonyl ylides (1a-c) gave polycyclic tetrahydrothiophene derivatives (5a-c) by a chemo- and stereoselective 1,3-dipolar cycloaddition. The 1,3-dipoles (1a-c) were generated by thermal elimination of nitrogen from the corresponding 2,5-dihydro-1,3,4-thiadiazoles (4a-c).

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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:19 Aug 2013 06:27
Last Modified:07 Dec 2017 22:00
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Polish State Committee for Scientific Research (Grant No. 3 TO9A 00716, Swiss National Science Foundation, F. Hoffmann-La roche AG, Basel
Publisher DOI:https://doi.org/10.3987/COM-02-S61

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