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2,4‐Didehydrophenol—First Proof of a meta ‐Aryne by IR Spectroscopy
Author(s) -
Bucher Götz,
Sander Wolfram,
Kraka Elfi,
Cremer Dieter
Publication year - 1992
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.199212301
Subject(s) - diradical , aryne , matrix isolation , chemistry , spectroscopy , infrared spectroscopy , decarboxylation , carbene , bicyclic molecule , computational chemistry , medicinal chemistry , photochemistry , organic chemistry , physics , atomic physics , excited state , singlet state , quantum mechanics , catalysis
Photochemical decarboxylation of carbene 1 in an argon matrix at 10 K provides 2,4‐didehydrophenol ( 2 ). This m ‐aryne was characterized by IR and UV/VIS spectroscopy; the experimental and the calculated (GVB/6‐31G(d,p)) IR spectra are in good agreement. These findings suggest that 2 has a diradical, mono‐cyclic structure; the isomeric bicyclic structure 3 can be ruled out.