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Thermal and Photochemical Reactions of 1,2‐Annelated Barrelenes and Hydrobarrelenes in the presence of transition‐metal carbonyls
Author(s) -
Trifonov Latchezar S.,
Orahovats Alexander S.
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720404
Subject(s) - chemistry , irradiation , transition metal , inert gas , photochemistry , inert , medicinal chemistry , metal carbonyl , metal , organic chemistry , catalysis , physics , nuclear physics
The [Co 2 (CO) 8 ]‐mediated retro ‐ Diels ‐ Alder reaction of the annelated barrelenes 1 afforded the 1 H ‐indol‐2(3 H )‐one derivatives 3 ( Scheme 1 ), while the hydrobarrelene 4a , under the same conditions, was converted to the anilide 6 ( Scheme 2 ); 4b remained unaffected. The direct irradiation of 1 led to the annelated cyclooctatetraenes 7 ( Scheme 3 ). On irradiation in the presence of excess of [Fe(CO) 5 ], 1a , 1b , and 4a gave the tricarbonyliron complexes 8 , 9 , and 11 , respectively ( Schemes 3 and 4 ); under these conditions, 4b was inert.