Mechanism of magnesium carbenoid 1,3‐C–H insertion: a DFT study | Zendy

Kimura Tsutomu | Zendy; Satoh Tsuyoshi | Zendy

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Mechanism of magnesium carbenoid 1,3‐C–H insertion: a DFT study

Author(s) -

Kimura Tsutomu,

Satoh Tsuyoshi

Publication year - 2015

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.3440

Subject(s) - carbenoid , chemistry , magnesium , sn2 reaction , electrophile , density functional theory , nucleophile , chloride , insertion reaction , medicinal chemistry , atom (system on chip) , computational chemistry , stereochemistry , organic chemistry , catalysis , rhodium , computer science , embedded system

The 1,3‐C–H insertion of magnesium carbenoid and related species was investigated via density functional theory (DFT) calculations. The 1,3‐C–H insertion occurred according to an S N 2‐like mechanism wherein the nucleophilic C–H bond attacked the electrophilic carbenoid carbon atom. The activation energies for the 1,3‐C–H insertion of (1‐chloropropyl)magnesium chloride, (1‐methoxypropyl)magnesium chloride, and [1‐(methylthio)propyl]magnesium chloride were 20.0, 33.8, and 47.1 kcal/mol, respectively. Copyright © 2015 John Wiley & Sons, Ltd.

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