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Direct Observation and Trapping of a Heterocyclic α‐Oxo Ketene: 3‐Carbonyl‐1,3‐dihydro‐1‐methyl‐2 H ‐indol‐2‐one
Author(s) -
Kappe Thomas,
Oliver Kappe C.,
Wentrup Curt,
Färber Gerald
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931261026
Subject(s) - ketene , chemistry , flash vacuum pyrolysis , trapping , methanol , mass spectrometry , pyrolysis , photochemistry , photodissociation , matrix isolation , spectroscopy , medicinal chemistry , infrared spectroscopy , organic chemistry , chromatography , ecology , physics , biology , quantum mechanics
The title compound 8a was generated by both flash vacuum pyrolysis and matrix photolysis of diazoquinolone 7 and identified by Ar‐matrix IR spectroscopy and mass spectrometry. Trapping of the highly reactive α‐oxo ketene 8a with methanol leads to β‐keto ester 9 , whereas dimerization of 8a furnishes spiro compound 10 .