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- Title
Cover Feature: S<sub>N</sub>2 Reaction of Diarylmethyl Anions at Secondary Alkyl and Cycloalkyl Carbons (Eur. J. Org. Chem. 7/2019).
- Authors
Shinohara, Riku; Ogawa, Narihito; Kawashima, Hidehisa; Wada, Kyohei; Saito, Shun; Yamazaki, Takashi; Kobayashi, Yuichi
- Abstract
The Cover Feature shows the substitution of cis 4‐tBu‐cyclohexyl diphenyl phosphate with Ph2CHLi (Real), which is completed in 15 min at –15 °C, whereas that of the trans isomer took 7 h. To understand the different reactivity, energy levels along the reaction coordinates of model reactions consisting of cis and trans dimethyl phosphates and MeLi (Model reaction) were calculated to find the lower TS energy for the cis isomer than that of the trans isomer. The inflated TS‐HOMO orbital of Me–Li (green) shows bond breaking and bond making of the substitution. More information can be found in the Full Paper by Y. Kobayashi et al.
- Subjects
BENZYLIC group; CYCLOALKYL group; NUCLEOPHILIC substitution reactions
- Publication
European Journal of Organic Chemistry, 2019, Vol 2019, Issue 7, p1419
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201900167