Transition states of the retro-ene reactions of allylic diazenes

Arash Jabbari; Erik J. Sorensen; K. N. Houk

doi:10.1021/ol0612049

Transition states of the retro-ene reactions of allylic diazenes

Arash Jabbari, Erik J. Sorensen, K. N. Houk

Chemistry

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

22 Scopus citations

Abstract

Density functional theory studies of intramolecular retro-ene reactions of allyldiazenes show that the reaction is a concerted process involving a six-center cyclic transition state. The activation barriers for deazetization for X = H, Me, F, Cl, and Br (3a-e) are 2.4, 40.2, 22.3, 9.3, and 8.8 kcal/mol, respectively.

Original language	English (US)
Pages (from-to)	3105-3107
Number of pages	3
Journal	Organic letters
Volume	8
Issue number	14
DOIs	https://doi.org/10.1021/ol0612049
State	Published - Jul 6 2006

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0612049

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abstract = "Density functional theory studies of intramolecular retro-ene reactions of allyldiazenes show that the reaction is a concerted process involving a six-center cyclic transition state. The activation barriers for deazetization for X = H, Me, F, Cl, and Br (3a-e) are 2.4, 40.2, 22.3, 9.3, and 8.8 kcal/mol, respectively.",

author = "Arash Jabbari and Sorensen, {Erik J.} and Houk, {K. N.}",

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AU - Sorensen, Erik J.

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N2 - Density functional theory studies of intramolecular retro-ene reactions of allyldiazenes show that the reaction is a concerted process involving a six-center cyclic transition state. The activation barriers for deazetization for X = H, Me, F, Cl, and Br (3a-e) are 2.4, 40.2, 22.3, 9.3, and 8.8 kcal/mol, respectively.

AB - Density functional theory studies of intramolecular retro-ene reactions of allyldiazenes show that the reaction is a concerted process involving a six-center cyclic transition state. The activation barriers for deazetization for X = H, Me, F, Cl, and Br (3a-e) are 2.4, 40.2, 22.3, 9.3, and 8.8 kcal/mol, respectively.

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Transition states of the retro-ene reactions of allylic diazenes

Abstract

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