Cycloaddition of vinyl aziridines with unsaturated substrates. A novel rearrangement of an unsaturated nitro compound.

Alfred Hassner; Rosario D'Costa; Andrew T. McPhail; William Butler

doi:10.1016/S0040-4039(01)81995-X

Cycloaddition of vinyl aziridines with unsaturated substrates. A novel rearrangement of an unsaturated nitro compound.

Alfred Hassner, Rosario D'Costa, Andrew T. McPhail, William Butler

Research output: Contribution to journal › Article › peer-review

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Abstract

Vinylaziridine 2 undergoes reaction with electrophilic acetylenes and olefins to produce 7-membered azepine derivatives. With β-nitro-styrene however, a novel rearrangement occurs, presumably via an ene reaction to form 10, the structure of which is definitively shown by x-ray diffraction.

Original language	English
Pages (from-to)	3691-3694
Number of pages	4
Journal	Tetrahedron Letters
Volume	22
Issue number	38
DOIs	https://doi.org/10.1016/S0040-4039(01)81995-X
State	Published - 1981
Externally published	Yes

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title = "Cycloaddition of vinyl aziridines with unsaturated substrates. A novel rearrangement of an unsaturated nitro compound.",

abstract = "Vinylaziridine 2 undergoes reaction with electrophilic acetylenes and olefins to produce 7-membered azepine derivatives. With β-nitro-styrene however, a novel rearrangement occurs, presumably via an ene reaction to form 10, the structure of which is definitively shown by x-ray diffraction.",

author = "Alfred Hassner and Rosario D'Costa and McPhail, {Andrew T.} and William Butler",

year = "1981",

doi = "10.1016/S0040-4039(01)81995-X",

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AU - Hassner, Alfred

AU - D'Costa, Rosario

AU - McPhail, Andrew T.

AU - Butler, William

PY - 1981

Y1 - 1981

N2 - Vinylaziridine 2 undergoes reaction with electrophilic acetylenes and olefins to produce 7-membered azepine derivatives. With β-nitro-styrene however, a novel rearrangement occurs, presumably via an ene reaction to form 10, the structure of which is definitively shown by x-ray diffraction.

AB - Vinylaziridine 2 undergoes reaction with electrophilic acetylenes and olefins to produce 7-membered azepine derivatives. With β-nitro-styrene however, a novel rearrangement occurs, presumably via an ene reaction to form 10, the structure of which is definitively shown by x-ray diffraction.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

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Cycloaddition of vinyl aziridines with unsaturated substrates. A novel rearrangement of an unsaturated nitro compound.

Abstract

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