Volume 21, Issue 16
Heterocyclic Compounds
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ChemInform Abstract: Generation and Cycloadditions of 2-(N-Acylamino)-1-thia-1,3-dienes. Part 2. Rationalization of Reactivity Using an FMO Approach.

I. T. BARNISH

I. T. BARNISH

Sch. Chem., Univ. Leeds, Leeds LS2 9JT, UK

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C. W. G. FISHWICK

C. W. G. FISHWICK

Sch. Chem., Univ. Leeds, Leeds LS2 9JT, UK

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D. R. HILL

D. R. HILL

Sch. Chem., Univ. Leeds, Leeds LS2 9JT, UK

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C. JUN. SZANTAY

C. JUN. SZANTAY

Sch. Chem., Univ. Leeds, Leeds LS2 9JT, UK

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First published: April 17, 1990

Abstract

Acylation of the thioamide (I) leads to the title dienes which undergo regiospecific and stereoselective Diels-Alder reactions with electron deficient and electron rich alkenes to give dihydrothiopyrans.

ChemInform Abstract

Acylation of the thioamide (I) leads to the title dienes which undergo regiospecific and stereoselective Diels-Alder reactions with electron deficient and electron rich alkenes to give dihydrothiopyrans. FMO calculations are carried out in order to rationalize the reactivity of the title dienes. The general trends which result from these calculations are in good agreement with the experimental observations.

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