Issue 15, 2022

Theoretical study of a derivative of chlorophosphine with aliphatic and aromatic Grignard reagents: SN2@P or the novel SN2@Cl followed by SN2@C?

Abstract

The proposed SN2 reactions of a hindered organophosphorus reactant with aliphatic and aromatic nucleophiles [Ye et al., Org. Lett., 2017, 19, 5384–5387] were studied theoretically in order to explain the observed stereochemistry of the products. Our computations (using B3LYP as the functional) indicate that the reaction with the aliphatic nucleophile occurs through a backside SN2@P pathway while the reaction with the aromatic nucleophile proceeds through a novel SN2@Cl mechanism, followed by a frontside SN2@C mechanism.

Graphical abstract: Theoretical study of a derivative of chlorophosphine with aliphatic and aromatic Grignard reagents: SN2@P or the novel SN2@Cl followed by SN2@C?

Supplementary files

Article information

Article type
Paper
Submitted
13 Jan 2022
Accepted
15 Mar 2022
First published
23 Mar 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 9130-9138

Theoretical study of a derivative of chlorophosphine with aliphatic and aromatic Grignard reagents: SN2@P or the novel SN2@Cl followed by SN2@C?

N. Savoo, L. Rhyman and P. Ramasami, RSC Adv., 2022, 12, 9130 DOI: 10.1039/D2RA00258B

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