3-pyridylcarbene and 3-pyridylnitrene: Ring opening to nitrile ylides

Bednarek, P. and Wentrup, C. (2003) 3-pyridylcarbene and 3-pyridylnitrene: Ring opening to nitrile ylides. Journal of The American Chemical Society, 125 30: 9083-9089. doi:10.1021/ja035632a


Author Bednarek, P.
Wentrup, C.
Title 3-pyridylcarbene and 3-pyridylnitrene: Ring opening to nitrile ylides
Journal name Journal of The American Chemical Society   Check publisher's open access policy
ISSN 0002-7863
Publication date 2003
Sub-type Article (original research)
DOI 10.1021/ja035632a
Volume 125
Issue 30
Start page 9083
End page 9089
Total pages 7
Place of publication U.S.A.
Publisher American Chemical Society
Collection year 2003
Language eng
Subject C1
250303 Physical Organic Chemistry
780103 Chemical sciences
0399 Other Chemical Sciences
Abstract Photolysis of 3-pyridyldiazomethane in an Ar matrix at 7-10 K gives 3-pyridylcarbene. Further photolysis causes ring opening to nitrile ylide 26 (formonitrile pent-2-en-4-ynylide) as the major reaction together with a minor amount of ring expansion to 1-azacyclohepta-1,3,4,6-tetraene, 27. Matrix photolysis of 3-azidopyridine leads to ring opening to formonitrile N-cyanovinylmethylide, 33.
Keyword Ab-initio
Carbene
Chemistry, Multidisciplinary
Density-functional Theory
Energy Surface
Expansion
Interconversion
Nitrene Rearrangements
Phenylcarbene
Phenylnitrene
Photochemistry
Q-Index Code C1

 
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Citation counts: TR Web of Science Citation Count  Cited 27 times in Thomson Reuters Web of Science Article | Citations
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Created: Wed, 15 Aug 2007, 01:34:52 EST