3-Pyridylnitrene, 2- and 4-pyrimidinylcarbenes, 3-quinolylnitrenes, and 4-quinazolinylcarbenes. Interconversion, ring expansion to diazacycloheptatetraenes, ring opening to nitrile ylides, and ring contraction to cyanopyrroles and cyanoindoles

3-Pyridylnitrene, 2- and 4-pyrimidinylcarbenes, 3-quinolylnitrenes, and 4-quinazolinylcarbenes. Interconversion, ring expansion to diazacycloheptatetraenes, ring opening to nitrile ylides, and ring contraction to cyanopyrroles and cyanoindoles

Precursors of 3-pyridylnitrene and 2- and 4-pyrimidinylcarbenes all afford mixtures of 2- and 3-cyanopyrroles on flash vacuum thermolysis, but 3-cyanopyrroles are the first-formed products. 3-Quinolylnitrenes and 4-quinazolinylcarbenes similarly afford 3-cyanoindoles. 2-Pyrimidinylcarbenes rearrange...

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Bibliographic Details
Main Authors: Curt Wentrup, Nguyen Mong Lan, Adelheid Lukosch, Pawel Bednarek, David Kvaskoff
Format: Article
Language:English
Published: Beilstein-Institut 2013-04-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
carbene-nitrene interconversion
diazepines
flash vacuum thermolysis
matrix photochemistry
nitrile ylides
reactive intermediates
Online Access:https://doi.org/10.3762/bjoc.9.84

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