On the Mechanism and Scope of a Novel Nitroolefin Rearrangement

Alfred Hassner; William Chau

doi:10.1016/s0040-4039(00)87241-x

On the Mechanism and Scope of a Novel Nitroolefin Rearrangement

Alfred Hassner, William Chau

State University of New York Binghamton University

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

22 Scopus citations

Abstract

D-Labelling permits differentiation between three plausible mechanistic pathways in the novel transformation of vinylaziridine 1 with β-nitrostyrene 4 to nitro enamino olefin 5. The results are consistent with a retro-ene reaction proceeding under mild conditions (80°). Choice of proper substituents can guide the reaction toward formation of azepines or substituted enamines.

Original language	English
Pages (from-to)	1989-1992
Number of pages	4
Journal	Tetrahedron Letters
Volume	23
Issue number	19
DOIs	https://doi.org/10.1016/s0040-4039(00)87241-x
State	Published - 1982
Externally published	Yes

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title = "On the Mechanism and Scope of a Novel Nitroolefin Rearrangement",

abstract = "D-Labelling permits differentiation between three plausible mechanistic pathways in the novel transformation of vinylaziridine 1 with β-nitrostyrene 4 to nitro enamino olefin 5. The results are consistent with a retro-ene reaction proceeding under mild conditions (80°). Choice of proper substituents can guide the reaction toward formation of azepines or substituted enamines.",

author = "Alfred Hassner and William Chau",

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doi = "10.1016/s0040-4039(00)87241-x",

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AB - D-Labelling permits differentiation between three plausible mechanistic pathways in the novel transformation of vinylaziridine 1 with β-nitrostyrene 4 to nitro enamino olefin 5. The results are consistent with a retro-ene reaction proceeding under mild conditions (80°). Choice of proper substituents can guide the reaction toward formation of azepines or substituted enamines.

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JO - Tetrahedron Letters

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On the Mechanism and Scope of a Novel Nitroolefin Rearrangement

Abstract

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