128333-12-0Relevant articles and documents
Synthesis of 2,6-Disubstituted Dihydronaphthalenes and Naphthalenes by Electrocyclic Reaction of o-Quinodimethane. A Synthesis of (+/-)-Naproxen
Shishido, Kozo,Yamashita, Akitake,Hiroya, Kou,Fukumoto, Keiichiro
, p. 469 - 475 (2007/10/02)
A survey of the electrocyclic reactions of o-quinodimethanes generated in situ by the thermolysis of dihydrobenzocyclobutenes with a variety of olefinic substituents at C-1 is reported.These reactions provide convenient access to the 2,6-disubstituted dihydronaphthalenes (11) and the naphthalenes (12).Thermolysis of the benzocyclobutenes (10) at 180 deg C in the presence of manganese dioxide affords in good yields the 2,6-di- and 2,3,6-tri-substituted naphthalenes (12) and (16).The naphthalenes (12b,f,h) thus obtained were easily converted into (+/-)-naproxen (5).