The retro-sulfolene reaction, which thermally produces 1,3-dienes from 2,5-dihydrothiophene-l,l-dioxides, is of considerable practical importance 1,2 interest. 3
Preparation of 2,3-dihetero-substituted 1,3-dienes from brominated 2-sulfolenes
โ Scribed by Chou, Ta Shue; Lee, Shwu Jiuan; Peng, Man Li; Sun, Der Jen; Chou, Shang Shing Peter
- Book ID
- 111946898
- Publisher
- American Chemical Society
- Year
- 1988
- Tongue
- English
- Weight
- 768 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0022-3263
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๐ SIMILAR VOLUMES
The title compounds were prepared by addition-elimination reactions of 2-(p-toluenesulfonyl)-2,3-butadien-l-01. The latter was readily obtained from 1,4-dichloro-2-butyne by selenosulfonation, reductive elimination of chlorine and [2,3] sigmatropic rearrangement of the corresponding selenoxide.
The geometryof dienesobtainedfrom2,3-substitutedsulfolenesbearinga 3-carboxyl derivativeis dependenton the natureof the 3-carboxygroupand on the functionalityof the 2substituent. These factorsthereforehavea crucialinfluenceon the stereoselectivityof subsequentDiels-Alderreactions, @ 1997Publishedby
Addition of (pseudo) halogens across the triple bond of 1,4-dichlorobut-2-yne, followed by a 1,4-elimination, provides a very simple preparation of ten novel butadienes. In recent years there has been a great deal of interest in asymmetrically substituted butadienes, both for theoretical reasons an