Formation of Four-membered rings Using the Intramolecular Wittig Reaction: Convenient Generation of Functionalised Butadienes

Robert Alan Aitken; ME Balkovich; HJ Bestmann; O Clem; Scott Gibson; T Röder

Formation of Four-membered rings Using the Intramolecular Wittig Reaction: Convenient Generation of Functionalised Butadienes

Robert Alan Aitken, ME Balkovich, HJ Bestmann, O Clem, Scott Gibson, T Röder

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

Abstract

Flash vacuum pyrolysis of the stable ylides 5, readily available by conjugate addition of ylides 3 to alpha,beta-unsaturated ketones 4, results in an intramolecular Wittig reaction with the delta-carbonyl to give cyclobutenes which under the conditions involved undergo electrocyclic ring-opening to afford the synthetically useful 1,3-dienes 7.

Original language	English
Pages (from-to)	1235-1236
Number of pages	2
Journal	Synlett
Publication status	Published - Aug 1999

Keywords

phosphorus ylides
Wittig reactions
flash pyrolysis
gas-phase chemistry
cycloadditions

Cite this

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title = "Formation of Four-membered rings Using the Intramolecular Wittig Reaction: Convenient Generation of Functionalised Butadienes",

abstract = "Flash vacuum pyrolysis of the stable ylides 5, readily available by conjugate addition of ylides 3 to alpha,beta-unsaturated ketones 4, results in an intramolecular Wittig reaction with the delta-carbonyl to give cyclobutenes which under the conditions involved undergo electrocyclic ring-opening to afford the synthetically useful 1,3-dienes 7.",

keywords = "phosphorus ylides, Wittig reactions, flash pyrolysis, gas-phase chemistry, cycloadditions",

author = "Aitken, \{Robert Alan\} and ME Balkovich and HJ Bestmann and O Clem and Scott Gibson and T R{\"o}der",

year = "1999",

month = aug,

language = "English",

pages = "1235--1236",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

}

TY - JOUR

T1 - Formation of Four-membered rings Using the Intramolecular Wittig Reaction: Convenient Generation of Functionalised Butadienes

AU - Aitken, Robert Alan

AU - Balkovich, ME

AU - Bestmann, HJ

AU - Clem, O

AU - Gibson, Scott

AU - Röder, T

PY - 1999/8

Y1 - 1999/8

N2 - Flash vacuum pyrolysis of the stable ylides 5, readily available by conjugate addition of ylides 3 to alpha,beta-unsaturated ketones 4, results in an intramolecular Wittig reaction with the delta-carbonyl to give cyclobutenes which under the conditions involved undergo electrocyclic ring-opening to afford the synthetically useful 1,3-dienes 7.

AB - Flash vacuum pyrolysis of the stable ylides 5, readily available by conjugate addition of ylides 3 to alpha,beta-unsaturated ketones 4, results in an intramolecular Wittig reaction with the delta-carbonyl to give cyclobutenes which under the conditions involved undergo electrocyclic ring-opening to afford the synthetically useful 1,3-dienes 7.

KW - phosphorus ylides

KW - Wittig reactions

KW - flash pyrolysis

KW - gas-phase chemistry

KW - cycloadditions

UR - https://www.scopus.com/pages/publications/0032791794

M3 - Article

SN - 0936-5214

SP - 1235

EP - 1236

JO - Synlett

JF - Synlett

ER -

Formation of Four-membered rings Using the Intramolecular Wittig Reaction: Convenient Generation of Functionalised Butadienes

Abstract

Keywords

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