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[3+2]-Photocycloadditions of dicyanonaphthalenes to alkenes

✍ Scribed by Yasuo Kubo; Masahiro Yoshioka; Kazuyuki Kiuchi; Satoshi Nakajima; Isamu Inamura

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
231 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

3+2]-Photocycloadditions of 1,2-, 1,3-, and 2,3-dicyanonaphthalenes to alkenes were found to proceed at the 1,8-, 4,5-, and 1,8-positions of the naphthalene ring of dicyanonaphthalenes, respectively. In the photoreactions of the 1,3-and 2,3-isomers [3+2]-adducts were obtained in oxidized forms and addition of Cu(OAc) z considerably improved the yields of the adducts. The observed addition sites of the alkenes are rationalized on the basis of the spin and charge densities of the radical anions of dicyanonaphthalenes.

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