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Homoallenyl radicals

✍ Scribed by J.K Crandall; G.L Tindell; A Manmade

Book ID
104221144
Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
267 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

Several homoallenyl radicals have been generated by the reaction of the corresponding iodides with BuaSnH and found to produce small amounts of vinylcyclopropanes in addition to allene hydrocarbons establishing that homoallenyl radicals cyclize to isomeric 1-cyclopropylvinyl radicals.

The interconversion of isomeric homoallyl (&) and cyclopropylcarbinyl (2) radicals has been the subject of considerable scrutiny.' Although this is not the situation in all molecular environments, it is generally true that 1 is favored over 2 by a considerable margin at equilibrium. Nonetheless, isomerization is kinetically rapid under most experimental conditions,3 resulting in interesting radical rearrangements in suitable instances.2 An intriguing variant of this system consists of the homoallenyl radical 3 and its cyclic isomer 4. Other possible

πŸ“œ SIMILAR VOLUMES

Additional evidence for homoallenyl part
Additional evidence for homoallenyl participation
✍ Thomas L. Jacobs; Roger Macomber πŸ“‚ Article πŸ“… 1967 πŸ› Elsevier Science 🌐 French βš– 220 KB

It wa8 recently reported(2) that a properly located allenyl system, , '(XX<, accelerated solvolysis more than a similarly located carbon-carbon double bond. Acetolysis of allenic brosylate Ia gave a first order rate constant (TABLE II) which was 19 times greater than that of 2,2-dimethyl-3-buten-l-y