Theoretical studies of carbenes and carbenoids. 5. Intramolecular reactions of cyclopropylcarbene

✍ Scribed by Bingze Wang; Conghao Deng

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 553 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)86230-x

✦ Synopsis

Intramolaculnr reaotions of cyclopropylcnrbono

tn sisglot grwnd 8tatc have beon studied using HF/34?tG gradient methods. Relative energies are eatimated with 6-31G**. The "super-con&:.tion" between the cyclopropyl and the p A0 at tho carbonc site stabilizes the carbene and retards ito cxo-endo ismerizuticn with a barrier of 13.7 kcal/aol.

The ring oxpansion occurs profornbly from the 0x0 confowatlon with a barrier of 12.3 kcal/nol. Two terminals disrotate in different rctatlon