Nitrile Ylides and Azirines: Gas‐Phase Generation from 2,3‐Dihydro‐1,4,λ 5 ‐oxazaphospholes and Matrix Isolation | Zendy

Wentrup Curt | Zendy; Fischer Stephan | Zendy; Berstermann HansMichael | Zendy; Kuzaj Martin | Zendy; Lüerssen Holger | Zendy; Burger Klaus | Zendy

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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).

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