UNUSUAL MONOSUBSTITUTION-MONODECHLORINATION PRODUCT IN THE REACTION OF 1,8-DICHLOROANTHRAQUINONE WITH (S)-(-)-2-(TETRAHYDROPYRANYLOXY)-1-PROPANOL

Authors
HABATA Y BRADSHAW JS NELSON RW IZATT RM
Citation
Y. Habata et al., UNUSUAL MONOSUBSTITUTION-MONODECHLORINATION PRODUCT IN THE REACTION OF 1,8-DICHLOROANTHRAQUINONE WITH (S)-(-)-2-(TETRAHYDROPYRANYLOXY)-1-PROPANOL, Tetrahedron, 53(12), 1997, pp. 4179-4184
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
12
Year of publication
1997
Pages
4179 - 4184
Database
ISI
SICI code
0040-4020(1997)53:12<4179:UMPITR>2.0.ZU;2-0
Abstract
Treatment of 1,8-dichloroanthraquinone with (S)-(-)-2-(tetrahydropyran yloxy)-1-propanol in the presence of NaH in THF gave monosubstitued-mo nodechlorinated product 2 and desired 1,8-disubstitued product 1. Mole cular mechanics calculations and H-1 NMR experiments suggest that the tetrahydropyranyl group in the side chain of monosubstituted-monochlor o product 3 hinders the second reaction site and the Na+ cation intera cts with the oxygen atoms of the side chain and ketone function allowi ng, the hydride anion access to the second reaction site. (C) 1997 Els evier Science Ltd.