ELECTRON-TRANSFER PHOTOCHEMISTRY OF 7-(SPIROCYCLOPROPANE)QUADRICYCLANE - CAPTURE OF A RADICAL-CATION AND SEQUENTIAL CYCLOPROPYLCARBINYL REARRANGEMENTS

Authors
MCILROY S WENG HX ROTH HD
Citation
S. Mcilroy et al., ELECTRON-TRANSFER PHOTOCHEMISTRY OF 7-(SPIROCYCLOPROPANE)QUADRICYCLANE - CAPTURE OF A RADICAL-CATION AND SEQUENTIAL CYCLOPROPYLCARBINYL REARRANGEMENTS, Journal of physical organic chemistry, 10(8), 1997, pp. 607-611
Citations number
22
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Journal of physical organic chemistry → ACNP
ISSN journal
08943230
Volume
10
Issue
8
Year of publication
1997
Pages
607 - 611
Database
ISI
SICI code
0894-3230(1997)10:8<607:EPO7>2.0.ZU;2-6
Abstract
The electron transfer photo-sensitized reaction of 7-(spiroeyclopropan e)quadricyclane (1) with methanol produces two rearranged mono-methano l adducts, 2 and 3, and abis-methanol adduct, 4. The products reveal t hat 1(.+) reacts by stereo-and regiospecific attack of methanol on one trisubstituted cyclopropane ring, The resulting free radical rapidly undergoes one or two (consecutive) cyctopropylcarbinyl to butenyl rear rangements. The mono-adducts are formed by net hydrogen abstraction, t he di-adduct via a (secondary) electron transfer reaction of 3. (C) 19 97 by John Wiley & Sons, Ltd.