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Die Struktur des Adduktes aus 3-Dimethylamino-2,2-dimethyl-2H-azirin und 3-Methyl-2,4-diphenyl-1,3-oxazolium-5-olat


Lukac, Josef; Bieri, Jost H; Heimgartner, Heinz (1977). Die Struktur des Adduktes aus 3-Dimethylamino-2,2-dimethyl-2H-azirin und 3-Methyl-2,4-diphenyl-1,3-oxazolium-5-olat. Helvetica Chimica Acta, 60(5):1657-1664.

Abstract

3-Dimethylamino-2,2-dimethyl-2H-azirine (1) reacts with 3-methyl-2,4-diphenyl-1,3-oxazolium-5-olate (5a) to give a 1:1 adduct (7) in 88% yield. Its crystal structure has been determined by X-ray analysis (direct methods) and refined with 1056 structure amplitudes to R = 0.032. The crystal system is monoclinic, space group P21/c, with unit cell dimensions a = 10.663, b = 9.828, c = 18.592 A, and beta = 90.63°. It is obvious that 4-dimethylamino-5,5-dimethyl-2-[alpha-(N-methylbenzamido)benzyliden]-delta3-1,3-oxazoline (7) arises from an addition of 1 to the valence-polaromeric ketene form 5b of the mesoionic oxazolone 5a (Scheme 3).

Abstract

3-Dimethylamino-2,2-dimethyl-2H-azirine (1) reacts with 3-methyl-2,4-diphenyl-1,3-oxazolium-5-olate (5a) to give a 1:1 adduct (7) in 88% yield. Its crystal structure has been determined by X-ray analysis (direct methods) and refined with 1056 structure amplitudes to R = 0.032. The crystal system is monoclinic, space group P21/c, with unit cell dimensions a = 10.663, b = 9.828, c = 18.592 A, and beta = 90.63°. It is obvious that 4-dimethylamino-5,5-dimethyl-2-[alpha-(N-methylbenzamido)benzyliden]-delta3-1,3-oxazoline (7) arises from an addition of 1 to the valence-polaromeric ketene form 5b of the mesoionic oxazolone 5a (Scheme 3).

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Additional indexing

Other titles:Structure of the adduct from 3-dimethylamino-2,2-dimethyl-2H-azirine and 3-methy1-2,4-diphenyl-1,3-oxazolium-5-olate
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1977
Deposited On:29 Oct 2014 12:55
Last Modified:05 Apr 2016 18:26
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
Publisher DOI:https://doi.org/10.1002/hlca.19770600521

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