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An Extremely Long‐Lived Triplet Carbene; Reactivity, Optical Absorption Spectrum, and Kinetics of Highly Congested Diarylcarbenes
Author(s) -
Tomioka Hideo,
Okada Hidetsumu,
Watanabe Tetsuya,
Hirai Katsuyuki
Publication year - 1994
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.199408731
Subject(s) - carbene , intramolecular force , diazo , photochemistry , reactivity (psychology) , kinetics , chemistry , absorption (acoustics) , absorption spectroscopy , medicinal chemistry , stereochemistry , materials science , organic chemistry , catalysis , physics , optics , medicine , alternative medicine , pathology , quantum mechanics , composite material
Half a second in solution at room temperature is the lifetime of didurylcarbene ( 1 ). This species is generated thermally and photochemically from the corresponding diazo compound and reacts by dimerization and by intramolecular H abstraction. The ortho methyl groups are key to stabilizing the carbene, and the meta methyl groups exert an additional buttressing effect.