The 5-hexenyl cyclization
β Scribed by Peter Schmid; David Griller; Keith U. Ingold
- Publisher
- John Wiley and Sons
- Year
- 1979
- Tongue
- English
- Weight
- 321 KB
- Volume
- 11
- Category
- Article
- ISSN
- 0538-8066
No coin nor oath required. For personal study only.
β¦ Synopsis
Abstract
The cyclization of the 5βhexenyl radical to form the cyclopentylmethyl radical has been reexamined by kinetic EPR spectroscopy at temperatures between 183 and 232Β°K in cyclopropane solvent. The rate constant, k~c~ for this important radical rearrangement can be represented by
where Ξ = 2.3__RT__ kcal/mol.
π SIMILAR VOLUMES
vs), 1156 (vs), 822 (m), 728 (m), and 547 (m) cm-l[3al. The vapor pressure curve accords with the equation log p = -1464/T+ 8.54 (Trouton constant 25.9).
Radical cyclization of 1-vinyl-5-methyl-5-hexenyl radicals (radical numbering) affords six-membered ring products prevailing over the isomeric five-membered ring compounds; the former are generated through two reaction pathways: 6-endo-trig ring closure and rearrangement of intermediate methylenecyc