Cover Feature: SN2 Reaction of Diarylmethyl Anions at Secondary Alkyl and Cycloalkyl Carbons (Eur. J. Org. Chem. 7/2019). Issue 7 (5th February 2019)

• Record Type: Journal Article
• Authors: Shinohara, Riku; Ogawa, Narihito; Kawashima, Hidehisa; Wada, Kyohei; Saito, Shun; Yamazaki, Takashi; Kobayashi, Yuichi
• Is Part Of: European journal of organic chemistry. Issue 7(2019)
• Page Start: 1419
• Page End: 1419
• Publication Date: 2019-02-05
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900167
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The Cover Feature shows the substitution of cis 4‐tBu‐cyclohexyl diphenyl phosphate with Ph2 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 theFull Paper by Y. Kobayashi et al.