Tetrahedron

Homolytic aziridine opening (aza variant of cyclopropylcarbinyl-homoallyl rearrangement) by addition of tributyltin radical to N-acylaziridines. Factors contributing to …

…, PY Lin, R Falkenstein, S Gries, H Irngartinger

Index: Werry, Juergen; Stamm, Helmut; Lin, Pen-Yuan; Falkenstein, Reinhard; Gries, Stefan; Irngartinger, Hermann Tetrahedron, 1989 , vol. 45, # 16 p. 5015 - 5028

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Citation Number: 2

Abstract

AIBN initiated reaction of N-acylaziridines 1 with Bu3SnH in refluxing benzene provided products 5 and 8 of reductive ring opening. Yields (practically quantitative in most cases) fell drastically with steric hindrance of the addition of Bu3Sn. to the acyl oxygen of 1. They depended to some extent on the experimental conditions for hydrogen capturing when aziridine homolysis provided a primary radical 3 or 6. The regioselectivity of (probably ...