Title

Structural Resolution Of The Stereochemistry Of A Spirooxirane Derived From An Alpha-Arylidene Heterocyclic Carbonyl - The Crystal And Molecular-Structure Of 2-(Para-Chlorophenyl)-5-Phenyl-7-Methyl-1-Oxa-5,6-Diazaspiro 2.4 Hept-6- En-4-One

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Abbreviated Journal Title

J. Heterocycl. Chem.

Keywords

Chemistry; Organic

Abstract

The stereochemical assignment of molecular geometry for α‐arylidene carbonyl compounds and spirooxirane derived from them have continued to be a challenging problem for which the most satisfactory solution continues to be an x‐ray diffraction structure determination. In that regard, the title compound (a spirooxirane) has been found to crystallize in the monoclinic space group P2 1/c with cell dimensions of a = 5.989(1)Å, b = 27.625(4)Å, c = 9.374(2)Å, β = 99.06(1)°. The structure of the compound has been determined, with the refinement to R = 0.059. The previous, tentative assignment of structure has been confirmed substantiating our prediction that the oxidation of the enone system proceeds with rotation of the phenyl group on the β‐carbon away from the carbonyl group, minimizing adverse steric interactions and allowing orbitals of the carbonyl group to overlap with those of the carbanionic center during the closure of the oxirane ring. The agreement between predictions based on nmr data and the x‐ray diffraction determination will support a stronger reliance on the nmr data predictions in subsequent studies.

Journal Title

Journal of Heterocyclic Chemistry

Volume

20

Issue/Number

3

Publication Date

1-2-1983

Document Type

Article

Language

English

First Page

559

Last Page

563

WOS Identifier

WOS:A1983QV68500014

ISSN

0022-152X

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