Citation
Ad. Allen et al., Generation, observation, and free radical reactivity of aliphatic bisketenes: The solution to a long-standing problem, ORG LETT, 3(25), 2001, pp. 4095-4098
Citations number
42
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060
→ ACNP
Volume
3
Issue
25
Year of publication
2001
Pages
4095 - 4098
Database
ISI
SICI code
1523-7060(200112)3:25<4095:GOAFRR>2.0.ZU;2-4
Abstract
[GRAPHICS]
Bisketenes O=C=CH(CH2)(n)CH=C=O (1b,c,d, n = 4, 3, 6) and (E)-O=C=CHCH=CHCH
=C=O (E-13) were generated in solution by dehydrochlorination of bis(acyl c
hlorides) and by photochemical Wolff rearrangements and identified by their
characteristic IR signals. The bisketenes react with aminoxyl radicals to
give tetraaddition products for lb and conjugate 1,6-diaddition for E-13.