Journal article

Publication year: 2011

Pages: 3526-3529

Journal: Organic Letters

Volume number: 13

Issue number: 13

DOI Link: https://doi.org/10.1021/ol2013457

Publisher: American Chemical Society

Abstract: 

We investigated both light- and heavy-atom tunneling in the rearrangements of a series of cyclopropylcarbenes using canonical variational transition state theory with multidimensional tunneling corrections (CVT/MT) and the Wentzel–Kramers–Brillouin (WKB) formalism. Halogeno- and hydroxy-substituted cyclopropylcarbenes were found not to undergo carbon tunneling owing to wide reaction barriers. However, while carbon tunneling plays a major role in the ring expansion of parent cyclopropylcarbene yielding cyclobutene, cyclopropylmethylcarbene is prone to undergo hydrogen tunneling to give cyclopropylmethylene.

Harvard Citation style: Gerbig, D., Ley, D. and Schreiner, P. (2011) Light- and Heavy-Atom Tunneling in Rearrangement Reactions of Cyclopropylcarbenes, Organic Letters, 13(13), pp. 3526-3529. https://doi.org/10.1021/ol2013457

APA Citation style: Gerbig, D., Ley, D., & Schreiner, P. (2011). Light- and Heavy-Atom Tunneling in Rearrangement Reactions of Cyclopropylcarbenes. Organic Letters. 13(13), 3526-3529. https://doi.org/10.1021/ol2013457