The duality in the cycloadditions of F-dimethylketene with cyclopropenones. A novel synthesis of unsymmetrical triafulvenes

I. Agranat; S. Cohen; E. Aharon-Shalom; E. D. Bergmann

doi:10.1016/0040-4020(75)85051-4

The duality in the cycloadditions of F-dimethylketene with cyclopropenones. A novel synthesis of unsymmetrical triafulvenes

I. Agranat^*
, S. Cohen
, E. Aharon-Shalom
, E. D. Bergmann

^*Corresponding author for this work

Institute of Chemistry

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

6 Scopus citations

Abstract

The reaction of F-dimethylketene 3 and diphenylcyclopropenone 7 in benzene solution affords 4-fluorocarbonyl-4-trifluoromethyl-1,2-diphenyltriafulvene 10. A mechanism of the cycloaddition through the intermediates F-methacryloyl fluoride 11 and the oxetane 12 is suggested. A contribution of the dipolar structure 10a is indicated. The cycloaddition of 3 and cyclopropenones constitutes a synthetic route to both symmetrical and unsymmetrical triafulvenes.

Original language	English
Pages (from-to)	1163-1165
Number of pages	3
Journal	Tetrahedron
Volume	31
Issue number	9
DOIs	https://doi.org/10.1016/0040-4020(75)85051-4
State	Published - 1975

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abstract = "The reaction of F-dimethylketene 3 and diphenylcyclopropenone 7 in benzene solution affords 4-fluorocarbonyl-4-trifluoromethyl-1,2-diphenyltriafulvene 10. A mechanism of the cycloaddition through the intermediates F-methacryloyl fluoride 11 and the oxetane 12 is suggested. A contribution of the dipolar structure 10a is indicated. The cycloaddition of 3 and cyclopropenones constitutes a synthetic route to both symmetrical and unsymmetrical triafulvenes.",

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AU - Cohen, S.

AU - Aharon-Shalom, E.

AU - Bergmann, E. D.

PY - 1975

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N2 - The reaction of F-dimethylketene 3 and diphenylcyclopropenone 7 in benzene solution affords 4-fluorocarbonyl-4-trifluoromethyl-1,2-diphenyltriafulvene 10. A mechanism of the cycloaddition through the intermediates F-methacryloyl fluoride 11 and the oxetane 12 is suggested. A contribution of the dipolar structure 10a is indicated. The cycloaddition of 3 and cyclopropenones constitutes a synthetic route to both symmetrical and unsymmetrical triafulvenes.

AB - The reaction of F-dimethylketene 3 and diphenylcyclopropenone 7 in benzene solution affords 4-fluorocarbonyl-4-trifluoromethyl-1,2-diphenyltriafulvene 10. A mechanism of the cycloaddition through the intermediates F-methacryloyl fluoride 11 and the oxetane 12 is suggested. A contribution of the dipolar structure 10a is indicated. The cycloaddition of 3 and cyclopropenones constitutes a synthetic route to both symmetrical and unsymmetrical triafulvenes.

UR - https://www.scopus.com/pages/publications/49549147952

U2 - 10.1016/0040-4020(75)85051-4

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JO - Tetrahedron

JF - Tetrahedron

IS - 9

ER -

The duality in the cycloadditions of F-dimethylketene with cyclopropenones. A novel synthesis of unsymmetrical triafulvenes

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