PHOTOCYCLIZATION REACTIONS OF EPOXY NITRILES VIA CARBONYL YLIDES - FORMATION OF SPIROKETALS, SPIROETHERS, AND A SPIROLACTONE

Authors
KOTERA M ISHII K SAKAMOTO M
Citation
M. Kotera et al., PHOTOCYCLIZATION REACTIONS OF EPOXY NITRILES VIA CARBONYL YLIDES - FORMATION OF SPIROKETALS, SPIROETHERS, AND A SPIROLACTONE, Chemical and Pharmaceutical Bulletin, 43(10), 1995, pp. 1621-1628
Citations number
14
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
43
Issue
10
Year of publication
1995
Pages
1621 - 1628
Database
ISI
SICI code
0009-2363(1995)43:10<1621:PROENV>2.0.ZU;2-4
Abstract
Photocyclization reactions (lambda = 254 nm) of gamma-methyl delta-(4- hydroxybutyl) and delta-(4-hydroxypentyl) alpha,beta-unsaturated gamma ,delta-epoxy nitriles gave spiroketals and spiroethers diastereoselect ively, whereas reaction of delta-(6-hydroxyhexyl) nitrile afforded no cyclization product, In addition, photocyclization of nitrite bearing a carboxyl group in the delta-side-chain afforded spirolactone.