REGIOSELECTIVITY IN PHOTOCYCLIZATION OF 2-(N,N-DIALKYLAMINO)ETHYL AND2-(N-ALKYLANILINO)ETHYL BENZOYLFORMATES VIA REMOTE PROTON-TRANSFER

Authors
HASEGAWA T YAMAZAKI Y
Citation
T. Hasegawa et Y. Yamazaki, REGIOSELECTIVITY IN PHOTOCYCLIZATION OF 2-(N,N-DIALKYLAMINO)ETHYL AND2-(N-ALKYLANILINO)ETHYL BENZOYLFORMATES VIA REMOTE PROTON-TRANSFER, Tetrahedron, 54(40), 1998, pp. 12223-12232
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
40
Year of publication
1998
Pages
12223 - 12232
Database
ISI
SICI code
0040-4020(1998)54:40<12223:RIPO2A>2.0.ZU;2-2
Abstract
Upon irradiation 2-(N,N-diallcylamino)- and 2-(N-alkylanilino)ethyl be nzoylformates 1 underwent photocyclization via zeta-hydrogen transfer to ketone carbonyl oxygen from charge-transfer states to give seven-me mbered azalactones 2 and/or 2'. The zeta-hydrogen transfer occurred re gioselectively. Neither Type II products produced via gamma-hydrogen t rasnfer nor five-membered aminolactones produced via delta-hydrogen tr ansfer could be detected. (C) 1998 Elsevier Science Ltd. All rights re served.