Photochemical generation of vinylketenes by electrocyclic opening of cyclobutenones

Alfred Hassner; Simha Naidorf

doi:10.1016/s0040-4039(00)87816-8

Photochemical generation of vinylketenes by electrocyclic opening of cyclobutenones

Alfred Hassner, Simha Naidorf

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

4,4-Dich1oro-2-cyclobutenones 1, available by cycloaddition of acetylenes to dichloroketene, can be photolyzed in the presence of olefins or dienes to produce regiospecifically 2-vinylcyclobutanones 3-11. The photochemical reaction succeeds even in some cases where thermolysis fails and was shown to proceed by electrocyclic ring opening to a vinylketene. Stereochemically the results of photolysis of 1 differ from thermolysis with identical olefinic substrates.

Original language	English
Pages (from-to)	6389-6392
Number of pages	4
Journal	Tetrahedron Letters
Volume	27
Issue number	52
DOIs	https://doi.org/10.1016/s0040-4039(00)87816-8
State	Published - 1986

Bibliographical note

Funding Information:
Support of this research by a grant from the Israel Academy of Sciences

Funding

Support of this research by a grant from the Israel Academy of Sciences

Funders	Funder number
Israel Academy of Sciences and Humanities

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10.1016/s0040-4039(00)87816-8

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title = "Photochemical generation of vinylketenes by electrocyclic opening of cyclobutenones",

abstract = "4,4-Dich1oro-2-cyclobutenones 1, available by cycloaddition of acetylenes to dichloroketene, can be photolyzed in the presence of olefins or dienes to produce regiospecifically 2-vinylcyclobutanones 3-11. The photochemical reaction succeeds even in some cases where thermolysis fails and was shown to proceed by electrocyclic ring opening to a vinylketene. Stereochemically the results of photolysis of 1 differ from thermolysis with identical olefinic substrates.",

author = "Alfred Hassner and Simha Naidorf",

note = "Funding Information: Support of this research by a grant from the Israel Academy of Sciences",

year = "1986",

doi = "10.1016/s0040-4039(00)87816-8",

language = "אנגלית",

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journal = "Tetrahedron Letters",

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T1 - Photochemical generation of vinylketenes by electrocyclic opening of cyclobutenones

AU - Hassner, Alfred

AU - Naidorf, Simha

N1 - Funding Information: Support of this research by a grant from the Israel Academy of Sciences

PY - 1986

Y1 - 1986

N2 - 4,4-Dich1oro-2-cyclobutenones 1, available by cycloaddition of acetylenes to dichloroketene, can be photolyzed in the presence of olefins or dienes to produce regiospecifically 2-vinylcyclobutanones 3-11. The photochemical reaction succeeds even in some cases where thermolysis fails and was shown to proceed by electrocyclic ring opening to a vinylketene. Stereochemically the results of photolysis of 1 differ from thermolysis with identical olefinic substrates.

AB - 4,4-Dich1oro-2-cyclobutenones 1, available by cycloaddition of acetylenes to dichloroketene, can be photolyzed in the presence of olefins or dienes to produce regiospecifically 2-vinylcyclobutanones 3-11. The photochemical reaction succeeds even in some cases where thermolysis fails and was shown to proceed by electrocyclic ring opening to a vinylketene. Stereochemically the results of photolysis of 1 differ from thermolysis with identical olefinic substrates.

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JO - Tetrahedron Letters

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IS - 52

ER -

Photochemical generation of vinylketenes by electrocyclic opening of cyclobutenones

Abstract

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