Base-induced ring closure of bis-dithioacetals via an apparent carbenoid. A novel route to functionalized cyclobutanes and cyclopentanes
✍ Scribed by Theodore Cohen; Daniel Ouellette; Wlodzimlerz M. Daniewski
- Book ID
- 104237428
- Publisher
- Elsevier Science
- Year
- 1978
- Tongue
- French
- Weight
- 231 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
A recent report from this laboratory disclosed an extremely efficient preparation of cyclopropanone dithioketals by treatment of dithioacetals containing a 3-phenylthio substituent with methyllithium in tetrahydrofuran (THF) containing tetramethylethylenediamine (TMEDA) at O'C. 1
We now report that remarkable ring closures to 4-and 5-membered rings occur when appropriate bis-dithioacetals are treated under the same conditions with four molar equivalents of methyllithium in THF containing four molar equivalents of TMEDA of methyllithium are used, the reaction is more sluggish. thio)hexane2 under the same conditions yields only ca. 5% other products of this reaction are under investigation. 3