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Additionen von 2,2-Dimethyl-3-dimethylamino-2H-azirin an 2-Formyl-cycloalkanone und Sulfinsäuren


Chandrasekhar, B Parthasarathi; Schmid, Ursula; Schmid, Rudolf; Heimgartner, Heinz; Schmid, Hans (1975). Additionen von 2,2-Dimethyl-3-dimethylamino-2H-azirin an 2-Formyl-cycloalkanone und Sulfinsäuren. Helvetica Chimica Acta, 58(4):1191-1200.

Abstract

2,2-Dimethyl-3-dimethylamino-2H-azirine (1) reacts with the formyl-cycloalkanones 4-8 in boiling benzene to give the 1:1 adducts 13-17 in 60-99% yield (Table). These adducts are N’-[(2-oxo-cycloalkylidene)methyl] derivatives of 2-amino-N,N-dimethylisobutyramide. The reaction mechanism (Scheme 6) is analogous to the mechanism of the reaction of 1 with carboxylic acids and cyclic enolisable 1,3-diketones [1]. Sulfinic acids and 1 undergo a similar reaction at - 15° to yield 2-sulfinamido-N,N-dimethylisobutyramides (Schemes 4 and 7), while sulfonic acids and the azirine 1 lead to a dimeric salt of type 20, which with sodium hydroxide gives the dihydropyrazine 21 (Scheme 5).

Abstract

2,2-Dimethyl-3-dimethylamino-2H-azirine (1) reacts with the formyl-cycloalkanones 4-8 in boiling benzene to give the 1:1 adducts 13-17 in 60-99% yield (Table). These adducts are N’-[(2-oxo-cycloalkylidene)methyl] derivatives of 2-amino-N,N-dimethylisobutyramide. The reaction mechanism (Scheme 6) is analogous to the mechanism of the reaction of 1 with carboxylic acids and cyclic enolisable 1,3-diketones [1]. Sulfinic acids and 1 undergo a similar reaction at - 15° to yield 2-sulfinamido-N,N-dimethylisobutyramides (Schemes 4 and 7), while sulfonic acids and the azirine 1 lead to a dimeric salt of type 20, which with sodium hydroxide gives the dihydropyrazine 21 (Scheme 5).

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1975
Deposited On:18 Nov 2014 15:04
Last Modified:05 Apr 2016 18:31
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
Publisher DOI:https://doi.org/10.1002/hlca.19750580423

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