INTRAMOLECULAR [3-ANNULATION OF OLEFIN-TETHERED CYCLOPROPYLAMINES(2])

Authors
HA JD LEE JW BLACKSTOCK SC CHA JK
Citation
Jd. Ha et al., INTRAMOLECULAR [3-ANNULATION OF OLEFIN-TETHERED CYCLOPROPYLAMINES(2]), Journal of organic chemistry, 63(23), 1998, pp. 8510-8514
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
23
Year of publication
1998
Pages
8510 - 8514
Database
ISI
SICI code
0022-3263(1998)63:23<8510:I[OOC>2.0.ZU;2-9
Abstract
Starting from readily available olefin-tethered tertiary aminocyclopro panes, we have developed a convenient [3 + 2] annulation reaction by m eans of one-electron oxidation which can be induced photochemically or chemically, followed by two sequential 5-exo radical cyclizations. Th e rate constants for the competing 1,5-hydrogen transfer in the beta-i mmonium carbon radical intermediate have been estimated to fall betwee n 1000 (6-exo) and 100 (7-exo and/or 8-endo) s(-1) at room temperature .