Contrasting regiochemistry in thermal and photochemical allylstannations of 1,2-naphthoquinone

Authors
Nishigaichi, Y Yoshida, N Matsuura, M Takuwa, A
Citation
Y. Nishigaichi et al., Contrasting regiochemistry in thermal and photochemical allylstannations of 1,2-naphthoquinone, CHEM LETT, (8), 1999, pp. 803-804
Citations number
22
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY LETTERS
ISSN journal
03667022 → ACNP
Issue
8
Year of publication
1999
Pages
803 - 804
Database
ISI
SICI code
0366-7022(199908):8<803:CRITAP>2.0.ZU;2-K
Abstract
1,2-Naphthoquinone with gamma-substituted allyltin reagents undergoes both thermal and photochemical reactions, which show the opposite regioselectivi ties to each other. The both reactions are supposed to proceed via the init ial 1,2-addition, which occurs at the gamma-position of the allyltin in the thermal reaction and at the less hindered alpha-position in the photoreact ion, followed by the [3,3] allylic migration.