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Cover Feature: S N 2 Reaction of Diarylmethyl Anions at Secondary Alkyl and Cycloalkyl Carbons (Eur. J. Org. Chem. 7/2019)
Author(s) -
Shinohara Riku,
Ogawa Narihito,
Kawashima Hidehisa,
Wada Kyohei,
Saito Shun,
Yamazaki Takashi,
Kobayashi Yuichi
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900167
Subject(s) - chemistry , reactivity (psychology) , alkyl , medicinal chemistry , cover (algebra) , reaction coordinate , substitution (logic) , computational chemistry , stereochemistry , organic chemistry , medicine , alternative medicine , pathology , mechanical engineering , computer science , engineering , programming language
The Cover Feature shows the substitution of cis 4‐tBu‐cyclohexyl diphenyl phosphate with Ph 2 CHLi (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.