Synthesis of Some 1-Azirines from -Bromo Ketoximes via Oxazaphospholines

Alfred Hassner; Vazken Alexanian

doi:10.1021/jo01336a024

Synthesis of Some 1-Azirines from -Bromo Ketoximes via Oxazaphospholines

Alfred Hassner
, Vazken Alexanian

State University of New York Binghamton University

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

37 Scopus citations

Abstract

A useful route from α-bromo ketoximes 1 to azirines is described which involves protection of 1 followed by phosphine substitution and deprotection via oxazaphospholine intermediates. The mild deprotection of the oxime ethers involves intramolecular assistance by a phosphonium group. New azirines, including a ring-deuterated species, have been synthesized.

Original language	English
Pages (from-to)	3861-3864
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	44
Issue number	22
DOIs	https://doi.org/10.1021/jo01336a024
State	Published - 1979
Externally published	Yes

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title = "Synthesis of Some 1-Azirines from -Bromo Ketoximes via Oxazaphospholines",

abstract = "A useful route from α-bromo ketoximes 1 to azirines is described which involves protection of 1 followed by phosphine substitution and deprotection via oxazaphospholine intermediates. The mild deprotection of the oxime ethers involves intramolecular assistance by a phosphonium group. New azirines, including a ring-deuterated species, have been synthesized.",

author = "Alfred Hassner and Vazken Alexanian",

year = "1979",

doi = "10.1021/jo01336a024",

language = "אנגלית",

volume = "44",

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journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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AU - Hassner, Alfred

AU - Alexanian, Vazken

PY - 1979

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AB - A useful route from α-bromo ketoximes 1 to azirines is described which involves protection of 1 followed by phosphine substitution and deprotection via oxazaphospholine intermediates. The mild deprotection of the oxime ethers involves intramolecular assistance by a phosphonium group. New azirines, including a ring-deuterated species, have been synthesized.

UR - https://www.scopus.com/pages/publications/0001464157

U2 - 10.1021/jo01336a024

DO - 10.1021/jo01336a024

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AN - SCOPUS:0001464157

SN - 0022-3263

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EP - 3864

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

Synthesis of Some 1-Azirines from -Bromo Ketoximes via Oxazaphospholines

Abstract

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