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


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.


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
Funding AgencyGrant Number
Record Number:CaltechTHESIS:02222016-113055066
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:9574
Deposited By: Leslie Granillo
Deposited On:23 Feb 2016 20:52
Last Modified:21 Dec 2019 03:52

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