22743-00-6Relevant articles and documents
Photoinduced electron-transfer reaction of α-bromomethyl-substituted benzocyclic β-keto esters with amines: Selective reaction pathways depending on the nature of the amine radical cations
Hasegawa, Eietsu,Tosaka, Emi,Yoneoka, Akira,Tamura, Yukinobu,Takizawa, Shin-Ya,Tomura, Masaaki,Yamashita, Yoshiro
, p. 247 - 267 (2013/03/13)
Photoinduced electron-transfer reaction of α-bromomethyl-substituted benzocyclic β-keto esters with tertiary amines was investigated. Debrominated β-keto esters and ring-expanded γ-keto esters were obtained as major products. On the basis of mechanistic experiments it was concluded that these products are formed via a reaction sequence of selective carbon-bromine bond cleavage and subsequent competitive hydrogen abstraction and Dowd-Beckwith ring-expansion of the resulting primary alkyl radicals. The characteristic product distribution observed for the type of amine used is rationalized on the basis of selective reaction pathways of generated radical intermediates that depend on the nature of the amine radical cations.
Photoreaction of halomethyl substituted benzocyclic ketones with amines: Radical cyclization and ring expansion reactions promoted through photoinduced electron transfer processes
Hasegawa, Eietsu,Tamura, Yukinobu,Tosaka, Emi
, p. 1895 - 1896 (2007/10/03)
Photoreaction of ethyl 2-bromomethyl-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 1a or other related compounds 1b-d with Me3SiCH2NEt2 in aqueous MeCN afforded ethyl 5-oxo-6,7,8,9-tetrahydrobenzocycloheptene-7-carboxylate 2a or corresponding ring expansion products 2a-d respectively.