Coupling of phenyllithium with trans- and cis-1-chloro-2-butene
โ Scribed by Magid, Ronald M.; Gandour, Richard D.
- Book ID
- 126437517
- Publisher
- American Chemical Society
- Year
- 1970
- Tongue
- English
- Weight
- 272 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0022-3263
No coin nor oath required. For personal study only.
๐ SIMILAR VOLUMES
Whereas sulfenyl reagents commonly add to carbon double bonds, addition to sulfur of 3-methylthio-1-butene precedes attack at carbon to give allylic thiosulfonium ions that form reversibly and which rearrange rapidly to trans-2-butenyl analogs. Likewise, rearrangement of cis-to trans-1-methylthio-2
H2S increases the thermal isomerization of butene-2 cis (B,) to butene-1 (B1) and butene-2 trans (Bt) around 500ยฐC. This effect is interpreted on the basis of a free radical mechanism in which buten-2-yl and thiyl free radicals are the main chain carriers. B1 formation is essentially explained by th