Reaction of Stabilised Phosphorus Ylides with Nitrogen Dioxide

Robert Alan Aitken; N Karodia

Reaction of Stabilised Phosphorus Ylides with Nitrogen Dioxide

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

4 Citations (Scopus)

Abstract

The reaction of the stabilised ylides 14-23 with an excess of NO2 in CH2Cl2 at room temperature gives different results depending on the structure of the starting ylide. The monacyl ylides 14-16 give the corresponding alpha-ore nitriles 4 together with Ph3PO . HNO3 (24) which has been fully characterised for the first time. Under the same conditions, the ylide 18 gives 2,4-dinitrobenzonitrile (26), Ph3PO, and benzoic acid. The other ylides examined all give 24 together with a variety of other products.

Original language	English
Pages (from-to)	251-254
Number of pages	4
Journal	European Journal of Organic Chemistry
Publication status	Published - Jan 1999

Keywords

phosphonium ylides
nitrogen dioxide
oxidation
nitriles
FLASH VACUUM PYROLYSIS
SELECTIVE OXIDATION
ALKYLIDENETRIPHENYLPHOSPHORANES
ALKYLENES

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title = "Reaction of Stabilised Phosphorus Ylides with Nitrogen Dioxide",

abstract = "The reaction of the stabilised ylides 14-23 with an excess of NO2 in CH2Cl2 at room temperature gives different results depending on the structure of the starting ylide. The monacyl ylides 14-16 give the corresponding alpha-ore nitriles 4 together with Ph3PO . HNO3 (24) which has been fully characterised for the first time. Under the same conditions, the ylide 18 gives 2,4-dinitrobenzonitrile (26), Ph3PO, and benzoic acid. The other ylides examined all give 24 together with a variety of other products.",

keywords = "phosphonium ylides, nitrogen dioxide, oxidation, nitriles, FLASH VACUUM PYROLYSIS, SELECTIVE OXIDATION, ALKYLIDENETRIPHENYLPHOSPHORANES, ALKYLENES",

author = "Aitken, {Robert Alan} and N Karodia",

year = "1999",

month = jan,

language = "English",

pages = "251--254",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

}

TY - JOUR

T1 - Reaction of Stabilised Phosphorus Ylides with Nitrogen Dioxide

AU - Aitken, Robert Alan

AU - Karodia, N

PY - 1999/1

Y1 - 1999/1

N2 - The reaction of the stabilised ylides 14-23 with an excess of NO2 in CH2Cl2 at room temperature gives different results depending on the structure of the starting ylide. The monacyl ylides 14-16 give the corresponding alpha-ore nitriles 4 together with Ph3PO . HNO3 (24) which has been fully characterised for the first time. Under the same conditions, the ylide 18 gives 2,4-dinitrobenzonitrile (26), Ph3PO, and benzoic acid. The other ylides examined all give 24 together with a variety of other products.

AB - The reaction of the stabilised ylides 14-23 with an excess of NO2 in CH2Cl2 at room temperature gives different results depending on the structure of the starting ylide. The monacyl ylides 14-16 give the corresponding alpha-ore nitriles 4 together with Ph3PO . HNO3 (24) which has been fully characterised for the first time. Under the same conditions, the ylide 18 gives 2,4-dinitrobenzonitrile (26), Ph3PO, and benzoic acid. The other ylides examined all give 24 together with a variety of other products.

KW - phosphonium ylides

KW - nitrogen dioxide

KW - oxidation

KW - nitriles

KW - FLASH VACUUM PYROLYSIS

KW - SELECTIVE OXIDATION

KW - ALKYLIDENETRIPHENYLPHOSPHORANES

KW - ALKYLENES

UR - http://www.scopus.com/inward/record.url?scp=0032784179&partnerID=8YFLogxK

M3 - Article

SN - 1434-193X

SP - 251

EP - 254

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

Reaction of Stabilised Phosphorus Ylides with Nitrogen Dioxide

Abstract

Keywords

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