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

23 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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10.1016/s0040-4039(00)87241-x

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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",

year = "1982",

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

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journal = "Tetrahedron Letters",

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AU - Chau, William

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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.

UR - https://www.scopus.com/pages/publications/0000157992

U2 - 10.1016/s0040-4039(00)87241-x

DO - 10.1016/s0040-4039(00)87241-x

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AN - SCOPUS:0000157992

SN - 0040-4039

VL - 23

SP - 1989

EP - 1992

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

On the Mechanism and Scope of a Novel Nitroolefin Rearrangement

Abstract

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