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S N 2 Reactions in Hydrocarbon Solvents Using Ammonium-Terminated Polyisobutylene Oligomers as Phase-Solubilizing Agents and Catalysts

S N 2 Reactions in Hydrocarbon Solvents Using Ammonium-Terminated Polyisobutylene Oligomers as Phase-Solubilizing Agents and Catalysts

Peerada Samunual, David E Bergbreiter

J Org Chem. 2018 Sep 21;83(18):11101-11107.

PMID: 30053377

Abstract:

Although SN2 reactions have been thoroughly studied in polar aprotic and protic solvents, not many studies have been done to study the rate of SN2 reaction in nonpolar solvents like alkanes due to the insolubility of anionic nucleophiles in these solvents. In this study, we investigated the use of N,N-diethyl- N-methylammonium-terminated polyisobutylene oligomers as phase-solubilizing agents for nucleophilic anions that could react with hydrocarbon-soluble substrates in alkanes. The results of these kinetic studies showed alkanes were comparable to MeCN as solvents in many reactions. Based on these studies, we developed a solid/liquid catalytic process using insoluble alkali metal carboxylate salts and a recyclable soluble polyisobutylene-bound catalyst that can be used to carry out SN2 reactions both in heptane and in hydrocarbon oligomeric solvents known as poly(α-olefins) (PAOs).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP9003274	Polyisobutylene		9003-27-4	Price

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