An isolable but highly reactive o-quinodimethane; 1,1a,2,3,4,4a-hexahydro-9,10-diphenyl-1,4-methanoanthracene
作者:David W. Jones、Alan Pomfret
DOI:10.1039/p19910000263
日期:——
The relatively stable o-quinodimethane 7 has been prepared by photodecarbonylation of the 1,3-diphenylinden-2-one-norbornene adduct 5. Reactions of 7 with phenyltriazolinedione, sulphur dioxide and triplet oxygen all occur to the less hindered face of the diene system terminating at the α,α′-positions of the o-quinodimethane. The same face of the same diene system is involved in forming the major carbonyl
相对稳定的邻喹啉甲烷7是通过1,3-二苯基茚满-2-一-降冰片烯加合物5的光脱羰制备的。7与苯基三唑啉二酮,二氧化硫和三重态氧的反应都发生在受阻较弱的二烯体系表面,终止于邻喹啉甲烷的α,α'-位置。相同的二烯系统的相同面参与形成主要羰基铁络合物,12,的7。热解和酸催化的7的重排均给出二氢萘10。1,5-σ氢位移7将产生10 在140°C下缓慢。