Development of a new method for the conversion of alcohols into chlorides

Author

Ian Addison McAlexander

Date of Award

12-1997

Degree Type

Thesis

Degree Name

Master of Science

Major

Chemistry

Major Professor

Ronald M. Magid

Abstract

A list of reagent systems is given below. Reagent systems (1) through (4) have been designed to afford as much unrearranged product as possible. The reactive intermediates of systems (2) through (5) are analogous to those of the Arbuzov reaction and will be discussed in Chapter 2.

(1) ROH + CH₃SO₂CI + LiCI in DMF/collidine ¹

(2) ROH + CH₃-S-CH₃ + N-chlorosuccinimide ²

(3) ROH + Ph₃P + CCI₄^{3, 4}

(4) ROH + Ph₃P + hexachloroacetone ^{5, 9}

(5) ROH + Ph₃P + diethylazodicarboxylate + HCI ⁶

The major goal of this work has been to find an efficient, mild method for converting alcohols into chlorides. Allylic alcohols provide a formidable challenge for any method and therefore help define the scope and usefulness of this reaction. The underlying logic in the choice of reagents came from analogy with the reactive intermediates in the reagent systems previously listed.

Recommended Citation

McAlexander, Ian Addison, "Development of a new method for the conversion of alcohols into chlorides. " Master's Thesis, University of Tennessee, 1997.
https://trace.tennessee.edu/utk_gradthes/10603