Synthesis, thermal reactivity, and kinetics of stabilized phosphorus ylides, part 2: [(Arylcarbamoyl)(cyano)-methylene]triphenylphosphoranes and their thiocarbamoyl analogues

R. Alan Aitken; Nouria A. Al-Awadi; Osman M. E. El-Dusouqui; Dorcas M. M. Farrell; Ajith Kumar

doi:10.1002/kin.20170

Synthesis, thermal reactivity, and kinetics of stabilized phosphorus ylides, part 2: [(Arylcarbamoyl)(cyano)-methylene]triphenylphosphoranes and their thiocarbamoyl analogues

R. Alan Aitken, Nouria A. Al-Awadi, Osman M. E. El-Dusouqui, Dorcas M. M. Farrell, Ajith Kumar

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

Abstract

A series of five cyano(arylcarbamoyl) phosphorus ylides 2 and five cyano(arylthiocarbamoyl) phosphorus ylides 3 are prepared and fully characterized. Pyrolytic reaction products of a representative example of each type obtained by flash vacuum pyrolysis technique show that they undergo thermal extrusion of Ph3PO or Ph3PS. Kinetic study of the gas-phase pyrolysis of each ylide by static method shows that these reactions are unimolecular and first order with no significant substituent effect, but the thiocarbamoyl ylides 3 react 40-65 times more rapidly than their carbamoyl analogues 2. (c) 2006 Wiley Periodicals, Inc.

Original language	English
Pages (from-to)	496-502
Number of pages	7
Journal	International Journal of Chemical Kinetics
Volume	38
DOIs	https://doi.org/10.1002/kin.20170
Publication status	Published - Aug 2006

Keywords

FLASH VACUUM PYROLYSIS
GAS-PHASE ELIMINATION
GAMMA-AMINO ACID
CARBOXYLIC-ACIDS
TERMINAL ALKYNES
WITTIG REAGENTS
ESTERS
ISOTHIOCYANATES
ISOCYANATES
DERIVATIVES

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@article{430313711d0b4662b1574ba2fb189521,

title = "Synthesis, thermal reactivity, and kinetics of stabilized phosphorus ylides, part 2: [(Arylcarbamoyl)(cyano)-methylene]triphenylphosphoranes and their thiocarbamoyl analogues",

abstract = "A series of five cyano(arylcarbamoyl) phosphorus ylides 2 and five cyano(arylthiocarbamoyl) phosphorus ylides 3 are prepared and fully characterized. Pyrolytic reaction products of a representative example of each type obtained by flash vacuum pyrolysis technique show that they undergo thermal extrusion of Ph3PO or Ph3PS. Kinetic study of the gas-phase pyrolysis of each ylide by static method shows that these reactions are unimolecular and first order with no significant substituent effect, but the thiocarbamoyl ylides 3 react 40-65 times more rapidly than their carbamoyl analogues 2. (c) 2006 Wiley Periodicals, Inc.",

keywords = "FLASH VACUUM PYROLYSIS, GAS-PHASE ELIMINATION, GAMMA-AMINO ACID, CARBOXYLIC-ACIDS, TERMINAL ALKYNES, WITTIG REAGENTS, ESTERS, ISOTHIOCYANATES, ISOCYANATES, DERIVATIVES",

author = "Aitken, {R. Alan} and Al-Awadi, {Nouria A.} and El-Dusouqui, {Osman M. E.} and Farrell, {Dorcas M. M.} and Ajith Kumar",

year = "2006",

month = aug,

doi = "10.1002/kin.20170",

language = "English",

volume = "38",

pages = "496--502",

journal = "International Journal of Chemical Kinetics",

issn = "0538-8066",

publisher = "John Wiley & Sons, Ltd",

}

Synthesis, thermal reactivity, and kinetics of stabilized phosphorus ylides, part 2: [(Arylcarbamoyl)(cyano)-methylene]triphenylphosphoranes and their thiocarbamoyl analogues. / Aitken, R. Alan; Al-Awadi, Nouria A.; El-Dusouqui, Osman M. E. et al.
In: International Journal of Chemical Kinetics, Vol. 38, 08.2006, p. 496-502.

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

TY - JOUR

T1 - Synthesis, thermal reactivity, and kinetics of stabilized phosphorus ylides, part 2: [(Arylcarbamoyl)(cyano)-methylene]triphenylphosphoranes and their thiocarbamoyl analogues

AU - Aitken, R. Alan

AU - Al-Awadi, Nouria A.

AU - El-Dusouqui, Osman M. E.

AU - Farrell, Dorcas M. M.

AU - Kumar, Ajith

PY - 2006/8

Y1 - 2006/8

N2 - A series of five cyano(arylcarbamoyl) phosphorus ylides 2 and five cyano(arylthiocarbamoyl) phosphorus ylides 3 are prepared and fully characterized. Pyrolytic reaction products of a representative example of each type obtained by flash vacuum pyrolysis technique show that they undergo thermal extrusion of Ph3PO or Ph3PS. Kinetic study of the gas-phase pyrolysis of each ylide by static method shows that these reactions are unimolecular and first order with no significant substituent effect, but the thiocarbamoyl ylides 3 react 40-65 times more rapidly than their carbamoyl analogues 2. (c) 2006 Wiley Periodicals, Inc.

AB - A series of five cyano(arylcarbamoyl) phosphorus ylides 2 and five cyano(arylthiocarbamoyl) phosphorus ylides 3 are prepared and fully characterized. Pyrolytic reaction products of a representative example of each type obtained by flash vacuum pyrolysis technique show that they undergo thermal extrusion of Ph3PO or Ph3PS. Kinetic study of the gas-phase pyrolysis of each ylide by static method shows that these reactions are unimolecular and first order with no significant substituent effect, but the thiocarbamoyl ylides 3 react 40-65 times more rapidly than their carbamoyl analogues 2. (c) 2006 Wiley Periodicals, Inc.

KW - FLASH VACUUM PYROLYSIS

KW - GAS-PHASE ELIMINATION

KW - GAMMA-AMINO ACID

KW - CARBOXYLIC-ACIDS

KW - TERMINAL ALKYNES

KW - WITTIG REAGENTS

KW - ESTERS

KW - ISOTHIOCYANATES

KW - ISOCYANATES

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=33746361182&partnerID=8YFLogxK

U2 - 10.1002/kin.20170

DO - 10.1002/kin.20170

M3 - Article

SN - 0538-8066

VL - 38

SP - 496

EP - 502

JO - International Journal of Chemical Kinetics

JF - International Journal of Chemical Kinetics

ER -

Synthesis, thermal reactivity, and kinetics of stabilized phosphorus ylides, part 2: [(Arylcarbamoyl)(cyano)-methylene]triphenylphosphoranes and their thiocarbamoyl analogues

Abstract

Keywords

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