Pyrolysis of Stabilised Phosphorus Ylides as a Route to New Hetero Carbenes

R Alan Aitken; M J  DRYSDALE; A  FORD; P E Y  MILNE; D W  RUSSELL; B M  RYAN; M  WHITTAKER

doi:10.1080/10426509308037357

Pyrolysis of Stabilised Phosphorus Ylides as a Route to New Hetero Carbenes

R Alan Aitken, M J DRYSDALE, A FORD, P E Y MILNE, D W RUSSELL, B M RYAN, M WHITTAKER

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Abstract

Flash vacuum pyrolysis of sulphonyl- and sulphinyl-stabilised phosphorus ylides results in loss of either phosphine or phosphine oxide to generate thio-, sulphinyl- and sulphonyl-carbenes which undergo a variety of rearrangement and insertion processes to give stable products. The first case of phosphine extrusion from a beta-oxo ylide is reported, giving access to benzotriazolyl acetyl carbene which rearranges to an acetyl benzotriazine and 2-cyanoacetophenone.

Original language	English
Pages (from-to)	31-34
Number of pages	4
Journal	Phosphorus, Sulfur, and Silicon and the Related Elements
Volume	75
Issue number	1-4
DOIs	https://doi.org/10.1080/10426509308037357
Publication status	Published - 1993

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FLASH VACUUM PYROLYSIS

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title = "Pyrolysis of Stabilised Phosphorus Ylides as a Route to New Hetero Carbenes",

abstract = "Flash vacuum pyrolysis of sulphonyl- and sulphinyl-stabilised phosphorus ylides results in loss of either phosphine or phosphine oxide to generate thio-, sulphinyl- and sulphonyl-carbenes which undergo a variety of rearrangement and insertion processes to give stable products. The first case of phosphine extrusion from a beta-oxo ylide is reported, giving access to benzotriazolyl acetyl carbene which rearranges to an acetyl benzotriazine and 2-cyanoacetophenone.",

keywords = "FLASH VACUUM PYROLYSIS",

author = "Aitken, \{R Alan\} and DRYSDALE, \{M J\} and A FORD and MILNE, \{P E Y\} and RUSSELL, \{D W\} and RYAN, \{B M\} and M WHITTAKER",

year = "1993",

doi = "10.1080/10426509308037357",

language = "English",

volume = "75",

pages = "31--34",

journal = "Phosphorus, Sulfur, and Silicon and the Related Elements",

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TY - JOUR

T1 - Pyrolysis of Stabilised Phosphorus Ylides as a Route to New Hetero Carbenes

AU - Aitken, R Alan

AU - DRYSDALE, M J

AU - FORD, A

AU - MILNE, P E Y

AU - RUSSELL, D W

AU - RYAN, B M

AU - WHITTAKER, M

PY - 1993

Y1 - 1993

N2 - Flash vacuum pyrolysis of sulphonyl- and sulphinyl-stabilised phosphorus ylides results in loss of either phosphine or phosphine oxide to generate thio-, sulphinyl- and sulphonyl-carbenes which undergo a variety of rearrangement and insertion processes to give stable products. The first case of phosphine extrusion from a beta-oxo ylide is reported, giving access to benzotriazolyl acetyl carbene which rearranges to an acetyl benzotriazine and 2-cyanoacetophenone.

AB - Flash vacuum pyrolysis of sulphonyl- and sulphinyl-stabilised phosphorus ylides results in loss of either phosphine or phosphine oxide to generate thio-, sulphinyl- and sulphonyl-carbenes which undergo a variety of rearrangement and insertion processes to give stable products. The first case of phosphine extrusion from a beta-oxo ylide is reported, giving access to benzotriazolyl acetyl carbene which rearranges to an acetyl benzotriazine and 2-cyanoacetophenone.

KW - FLASH VACUUM PYROLYSIS

UR - https://www.scopus.com/pages/publications/0347435176

U2 - 10.1080/10426509308037357

DO - 10.1080/10426509308037357

M3 - Article

SN - 1042-6507

VL - 75

SP - 31

EP - 34

JO - Phosphorus, Sulfur, and Silicon and the Related Elements

JF - Phosphorus, Sulfur, and Silicon and the Related Elements

IS - 1-4

ER -

Pyrolysis of Stabilised Phosphorus Ylides as a Route to New Hetero Carbenes

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