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

✍ Scribed by B. Parthasarathi Chandrasekhar; Ursula Schmid; Rudolf Schmid; Heinz Heimgartner; Hans Schmid

Publisher
John Wiley and Sons
Year
1975
Tongue
German
Weight
590 KB
Volume
58
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

2,2‐Dimethyl‐3‐dimethylamino‐2__H__‐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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