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Alkylation of Ketones with 3-Bromomethyl-l,2-Benzisothiazoles

Citation

Gillham, Robert Allen (1969) Alkylation of Ketones with 3-Bromomethyl-l,2-Benzisothiazoles. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/M56P-Z605. https://resolver.caltech.edu/CaltechTHESIS:02222016-113055066

Abstract

The synthesis of 3-bromomethyl-1,2-benzisothiazole and its 5- and 7-methoxy derivatives has been accomplished. In alkylation reactions, these bromides were found to behave much like benzylic bromides; and in this respect they have been used successfully to alkylate strongly basic enolates, thus introducing a latent β-phenylethyl moiety in situations where β-phenylethyl bromide and phenacyl bromide give at best poor yields of alkylated product. In several cases, degradative procedures have been devised to remove the heteroatoms from the benzisothiazoyl system to provide the actual β-phenylethyl fragment; however, no generally applicable degradative method has yet been developed.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Ireland, Robert E.
Thesis Committee:
  • Unknown, Unknown
Defense Date:26 May 1969
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
Record Number:CaltechTHESIS:02222016-113055066
Persistent URL:https://resolver.caltech.edu/CaltechTHESIS:02222016-113055066
DOI:10.7907/M56P-Z605
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:9574
Collection:CaltechTHESIS
Deposited By: Leslie Granillo
Deposited On:23 Feb 2016 20:52
Last Modified:21 Dec 2019 03:52

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