75391-24-1Relevant academic research and scientific papers
Nucleofugality effects in the pyridine promoted formation of esters from 2-substituted ethanesulfonyl chlorides
King, James Frederick,Hillhouse, John Henry,Lauriston, Toyanne Marie,Khemani, Kishan Chand
, p. 1109 - 1116 (2007/10/02)
The products of reaction of a series of 10 2-substituted ethanesulfonyl chlorides X-CH2CH2SO2Cl (1), with neopentyl alcohol and pyridine-d5 in nitromethane-d3 showed three reaction pathways depending on the nucleofugality of the substituent, X.These route
Organic sulfur mechanisms. 24. Preparation and reaction of 2-hydroxyethanesulfonyl chloride, the first hydroxyalkanesulfonyl chloride
King, James Frederick,Hillhouse, John Henry
, p. 1583 - 1593 (2007/10/02)
2-Hydroxyethanesulfonyl chloride (1a) is readily made by reaction of an aqeous solution of 2-mercaptoethanol (4a) with chlorine.This is the first clearly proved preparation of a compound which is both an alcohol and a sulfonyl chloride.Reactions of 1a with water and alcohols evidently proceed largely by intramolecular cyclization to the transient β-sultone (2a), which then undergoes nucleophilic ring opening to form the products.In the presence of tertiary amines a minor but significant part of the reaction is shown by deuterium labelling to proceed via hydroxymethylsulfene (14), the principal reaction of which is simply to add the alcohol or water; only a small part, if any, of the sulfene (14) loses the hydroxyl group to give the ethenesulfonate derivatives (13 or 22).Aqueous chlorination of 3-mercapto-1-propanol gave 3-chloro-1-propanesulfonyl chloride (5a) and 1,3-propane sultone (2b) with no sign of any 3-hydroxy-1-propanesulfonyl chloride (1b).A mechanism for the aqueous chlorination process invoking a cyclic chlorooxasulfoxonium ion (27) is discussed.
