Photochemical transformations. Part XXIX. Steric compression effects in the synthesis and reactions of 4-amino-5-methylphenanthrene
作者:D. H. R. Barton、P. G. Sammes、G. G. Weingarten
DOI:10.1039/j39710000729
日期:——
8-octahydrophenanthrene. The Semmler aromatisation reaction of this and related compounds was investigated and applied to the formation of 4-amino-5-methylphenanthrene. Alternative routes commencing from pyrene always gave internal cyclisation products caused by steric compression between the phenanthrene substituents at position 4 and 5. A useful variant of a Lossen-type reaction of dicarboxylic acid oxime toluene-p-sulphonates
对4-羟基-4-甲基-1,2,3,4,5,6,7,8-八氢菲的亚硝酸酯进行光解,得到4-羟基-5-羟基亚氨基-4-甲基-1,2,3 ,4,5,6,7,8-八氢菲。研究了该化合物和相关化合物的Semmler芳构化反应,并将其应用于4-氨基-5-甲基菲的形成。从pyr开始的替代途径总是产生内部环化产物,这是由于位置4和5上的菲取代基之间的空间压缩而引起的。这些化合物据报道是二羧酸肟甲苯-对-磺酸酯的Lossen型反应的有用变体。