ChemInform Abstract: Metalated Epoxides as Carbenoids. Solvent Effect on the Alkyl 1,2-Shift in α-Hydroxy Epoxide Systems.

✍ Scribed by E. DORIS; C. MIOSKOWSKI; L. DECHOUX; C. AGAMI

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199845097

✦ Synopsis

Metalated Epoxides as Carbenoids. Solvent Effect on the Alkyl 1,2-Shift in α-Hydroxy Epoxide Systems.

-The BuLi-mediated carbenoid alkyl 1,2-rearrangement of the deuterated α-hydroxy epoxide (I) is investigated in detail. The process is strongly affected by solvation of the lithium atoms, which is decisive in the regiochemical outcome of the reaction.