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- Title
Additionsreaktionen von 3-Dimethylamino-2,2-dimethyl-2 H-azirin an Phenylisocyanat und Diphenylketen.
- Authors
Mukherjee-Müller, Gabriele; Heimgartner, Heinz; Schmid, Hans
- Abstract
Addition Reaction of 3-Dimethylamino-2,2-dimethyl-2 H-azirine with Phenylisocyanate and Diphenylketene 3-Dimethylamino-2,2-dimethyl-2 H-azirine ( 1a) reacts with carbon disulfide and isothiocyanates with splitting of the azirine N(1), C(3)-double bond to give dipolar, fivemembered heterocyclic 1:1 adducts. In some cases, these products can undergo secondary reactions to yield 1:2 and 1:3 adducts. In this paper it is shown that the reaction of 1a with phenylisocyanate also takes place by cleavage of the N(1), C(3)-bond, whereas with diphenylketene N(1), C(2)-splitting is observed. The reaction of 1a and phenylisocyanate in hexane at room temperature yields the 1:3 adduct 2 in addition to the trimeric isocyanate 3 (Scheme 1). A mechanism for the formation of 2 is given in Scheme 5. Hydrolysis experiments with the 1:3 adduct 2, yielding the hydantoins 4-6 and the ureas 7 and 8 ( Schemes 3 and 5), show that the formation of this adduct via the intermediates d, e and f is a reversible reaction. The aminoazirines 1a and 1b undergo an addition reaction with diphenylketene to give the 3-oxazolines 14 (Scheme 8), the structure of which has been established by spectral data and oxidative degradation of 14a to the 3-oxazolin-2-one 15 (R1 R2 CH3, Scheme 9).
- Publication
Helvetica Chimica Acta, 1979, Vol 62, Issue 5, p1429
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19790620507