STUDIES IN ORGANOSULFUR CHEMISTRY.

Title: STUDIES IN ORGANOSULFUR CHEMISTRY.
Identifier: AAI8302535
identifier: 8302535
Creator: NICHOLAS, ELAINE C.
Contributor: W. F. Berkowitz
Date: 1982
Language: English
Publisher: City University of New York.
Subject: Chemistry, Organic
Abstract: The reaction of NBS, dry DMSO and alkenes to produce bromo ketones was explored. Conditions were sought in which the amount of dibromide would be reduced (varying time, temperature, addition of additives such as alkyltrimethylammonium tetrafluorborate resins, etc.). Yields for the reaction with cyclohexene were 18% of 2-bromocyclohexanone and 13% of 1,2-dibromocyclohexane. Instead of using DMSO, different amine oxides were tried. The best results were obtained using quinuclidine oxide which gave upon reaction with cyclohexene 47% of 2-bromocyclohexanone and 6% of 1,2-dibromocyclohexane.;Explorations were made into the synthesis and use of tosylmethyl THP ether as an acyl anion equivalent. It was synthesized from toluenesulfinic acid and formalin to give tosylmethanol (88%) which was treated with dihydropyran (using pyridinium toluenesulfinate as a weak acid catalyst) to give tosylmethyl THP ether (67%). This was reacted with alkyl halides (octyl bromide, benzyl bromide, cinnamyl bromide) and then hydrolyzed to give the corresponding aldehyde plus one additional carbon in good yield.
Type: dissertation
Source: PQT Legacy CUNY.xlsx
degree: Ph.D.
Program: Chemistry