THIOL-MEDIATED FREE-RADICAL CYCLIZATION OF ALKENYL AND ALKYNYL ISOCYANIDES

MD BACHI; A BALANOV; N BARNER

doi:10.1021/jo00104a035

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THIOL-MEDIATED FREE-RADICAL CYCLIZATION OF ALKENYL AND ALKYNYL ISOCYANIDES

Journal article

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THIOL-MEDIATED FREE-RADICAL CYCLIZATION OF ALKENYL AND ALKYNYL ISOCYANIDES

MD BACHI, A BALANOV and N BARNER

Journal of Organic Chemistry, Vol.59(25), pp.7752-7758

Dec/1994

DOI: https://doi.org/10.1021/jo00104a035

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Abstract

Thiol-mediated free radical cyclizations of but-3-enyl and but-3-ynyl isocyanides of types 6-8 give new access to 3,5-disubstituted 2-(alkyl- and 2-(arylthio)pyrrolines 11, 12, and 18. When 2-mercaptoethanol is used with the same isocyanides the reaction results in pyroglutamates 16, 17, or 19. These cyclizations involve the formation of a new carbon-carbon bond through intramolecular addition of a carbon-centered thioimidoyl radical to a carbon-carbon multiple bond. Although cyclic products are usually obtained in high yields, in a few cases a competing radical degradation process leading to isothiocyanates was observed. Isocyanide 8a carrying an allyl(phenyl) sulfide moiety isomerizes to 2-(phenylthio)pyrroline 24 in a series of sequential steps.

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Title: THIOL-MEDIATED FREE-RADICAL CYCLIZATION OF ALKENYL AND ALKYNYL ISOCYANIDES
Creators: MD BACHI (null)
A BALANOV (null)
N BARNER (null)
Resource Type: Journal article
Publication Details: Journal of Organic Chemistry, Vol.59(25), pp.7752-7758; Dec/1994
Number of pages: 7
Language: English
DOI: https://doi.org/10.1021/jo00104a035
Scientific Unit: The Weizmann Institute of Science
Record Identifier: 993265633603596

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