A theoretical study of the [4 + 4] dimerization of thioformylketene

Dhandapani V. Sadasivam; David M. Birney

doi:10.1021/ol052307e

A theoretical study of the [4 + 4] dimerization of thioformylketene

Dhandapani V. Sadasivam, David M. Birney

Chemistry and Biochemistry

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11 Scopus citations

Abstract

(Figure Presented) A theoretical study (B3LYP and G3MP2B3) of the dimerization of thioformylketene (1) was performed. Four pathways - two [4 + 2] pathways with thioformylketene (1), one [4 + 4] pathway with 1, and one [4 + 2] pathway involving 1 and thietone (11) - were considered. Interestingly, the [4 + 4] pathway with 1 had the lowest barrier (3.8 kcal/mol). The geometry of the transition state TS14 is unusual, with the forming bonds in the plane of the ketene. This suggests that the reaction is pseudopericyclic.

Original language	English
Pages (from-to)	5817-5820
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	26
DOIs	https://doi.org/10.1021/ol052307e
State	Published - Dec 22 2005

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title = "A theoretical study of the [4 + 4] dimerization of thioformylketene",

abstract = "(Figure Presented) A theoretical study (B3LYP and G3MP2B3) of the dimerization of thioformylketene (1) was performed. Four pathways - two [4 + 2] pathways with thioformylketene (1), one [4 + 4] pathway with 1, and one [4 + 2] pathway involving 1 and thietone (11) - were considered. Interestingly, the [4 + 4] pathway with 1 had the lowest barrier (3.8 kcal/mol). The geometry of the transition state TS14 is unusual, with the forming bonds in the plane of the ketene. This suggests that the reaction is pseudopericyclic.",

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AU - Sadasivam, Dhandapani V.

AU - Birney, David M.

PY - 2005/12/22

Y1 - 2005/12/22

N2 - (Figure Presented) A theoretical study (B3LYP and G3MP2B3) of the dimerization of thioformylketene (1) was performed. Four pathways - two [4 + 2] pathways with thioformylketene (1), one [4 + 4] pathway with 1, and one [4 + 2] pathway involving 1 and thietone (11) - were considered. Interestingly, the [4 + 4] pathway with 1 had the lowest barrier (3.8 kcal/mol). The geometry of the transition state TS14 is unusual, with the forming bonds in the plane of the ketene. This suggests that the reaction is pseudopericyclic.

AB - (Figure Presented) A theoretical study (B3LYP and G3MP2B3) of the dimerization of thioformylketene (1) was performed. Four pathways - two [4 + 2] pathways with thioformylketene (1), one [4 + 4] pathway with 1, and one [4 + 2] pathway involving 1 and thietone (11) - were considered. Interestingly, the [4 + 4] pathway with 1 had the lowest barrier (3.8 kcal/mol). The geometry of the transition state TS14 is unusual, with the forming bonds in the plane of the ketene. This suggests that the reaction is pseudopericyclic.

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U2 - 10.1021/ol052307e

DO - 10.1021/ol052307e

M3 - Article

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VL - 7

SP - 5817

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JO - Organic Letters

JF - Organic Letters

IS - 26

ER -

A theoretical study of the [4 + 4] dimerization of thioformylketene

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