Tetrahedron p. 565 - 576 (1987)
Update date:2022-09-26
Topics:
Onistschenko, Andreas
Buchholz, Berthold
Stamm, Helmut
Reaction of activated 2,2-dimethylaziridines 1 with Grignard reagents RMgHal in boiling THF can yield the products 2 of normal aziridine ring opening, the rearranged opening products 3, and the methallylamides 4 (isomers of 1 ). The product distribution depends on R, Hal, and experimental conditions, and very strongly on the nature of the activating group A. It is shown that 1 is opened (reversibly for A = sulfonyl) forming 10 through a Lewis acid assisted attack of Halθ on the tert carbon of 1 (abnormal opening by Halθ ). Evidence is presented to show that 4 as well as 3 come from this intermediate.
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