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Photoinduced Reactions of Cr(CO) 3 ‐Coordinated 1,3,5‐Cycloheptatriene: [6 + 2] Cycloaddition with an Alkyne and Catalytic 1,6‐Hydrogenation
Author(s) -
Fischler Ingrid,
Grevels FriedrichWilhelm,
Leitich Johannes,
Özkar Saim
Publication year - 1991
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.19911241229
Subject(s) - cycloheptatriene , trimethylsilyl , chemistry , alkyne , cycloaddition , medicinal chemistry , bicyclic molecule , ligand (biochemistry) , photochemistry , catalysis , organic chemistry , biochemistry , receptor
Irradiation of Cr(CO) 3 (η 6 ‐1,3,5‐cycloheptatriene) ( 1 ) in the presence of bis(trimethylsilyl)ethyne results in [6 + 2] cycloaddition of the alkyne to the cycloheptatriene ligand, yielding Cr(CO) 3 (η 4:2 ‐7,8‐bis(trimethylsilyl)bicyclo[4.2.1]nona‐2,4,7‐triene} ( 2 , 60% yield, Φ=0.08), which upon oxidative decomposition with Ce(IV) releases the organic cycloadduct, 7,8‐bis‐(trimethylsilyl)bicyclo[4.2.1]‐nona‐2,4,7‐triene ( 3 ). Photocatalytic hydrogenation of 1,3,5‐cycloheptatriene in the presence of complex 1 affords 1,3‐cycloheptadiene. This process involves 1,6‐addition of hydrogen, as demonstrated by using D 2 .