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Nitrile Ylides and Azirines: Gas‐Phase Generation from 2,3‐Dihydro‐1,4,λ 5 ‐oxazaphospholes and Matrix Isolation
Author(s) -
Wentrup Curt,
Fischer Stephan,
Berstermann HansMichael,
Kuzaj Martin,
Lüerssen Holger,
Burger Klaus
Publication year - 1986
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198600851
Subject(s) - nitrile , matrix isolation , flash vacuum pyrolysis , ylide , pyrolysis , azirine , gas phase , ring (chemistry) , chemistry , photochemistry , materials science , medicinal chemistry , organic chemistry , infrared spectroscopy
A thermally generated nitrile ylide has been directly observed for the first time: Pyrolysis of 1 at 700°C leads to the nitrile ylide 2 (sharp IR band at v = 2250 cm −1 ). The flash pyrolysis of 1 at 400°C, on the other hand, furnishes the azirine 3 , the ring of which opens upon irradiation to give 2 (R = t Bu).