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Synthesis and reactions of poly[(4-chlorobutyl)thiirane]: evidence for backbone-assisted solvolysis

Shih, Jenn S. and Tirrell, David A. (1984) Synthesis and reactions of poly[(4-chlorobutyl)thiirane]: evidence for backbone-assisted solvolysis. Chemical Engineering Communications, 30 (3-5). pp. 219-228. ISSN 0098-6445. doi:10.1080/00986448408911129.

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(4-Chlorobutyl)thiirane is prepared in 80% yield in a single step from (4-chlorobutyl)oxirane. Homopolymerization of (4-chlorobutyl)thiirane with ZnEt2—CH3OH or CdCO3 initiator systems provides poly[(4-chlorobutyl)thiirane] as a soft elastomer with inherent viscosity 0.2dL/g. Reaction of poly[(4-chlorobutyl)thiirane] with tetra-n-butylammonium benzoate in N,N-dimethylacetamide proceeds by direct displacement, without involvement of the backbone sulfur atom. Solvolysis under more strongly ionizing conditions (acetic acid/chloroform) occurs with repeating unit isomerization, most probably via a cyclic intermediate formed by attack of the backbone sulfur atom on the chloromethyl group at the side chain terminus.

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Tirrell, David A.0000-0003-3175-4596
Additional Information:© 1984 Gordon & Breach. (Received February 16, 1984; in final form March 19, 1984) Dedicated to Professor E. W. Merrill on the occasion of his 60th birthday, with best wishes. This work was supported by an Alfred P. Sloan Research Fellowship to David A. Tirrell and by a grant from the Polymers Program of the National Science Foundation (DMR82-01180). The Bruker WM-300 spectrometer was purchased with the aid of a grant from the National Institutes of Health (GM27390). NMR spectra at 600 MHz were recorded at the NIH NMR Facility for Biomedical Studies (RR00292).
Funding AgencyGrant Number
Alfred P. Sloan FoundationUNSPECIFIED
NSFDMR 82-01180
Subject Keywords:Solvolysis, (4-chlorobutyl)thtirane, (4-chlorobutyl)oxirane, Polythiiranes
Issue or Number:3-5
Record Number:CaltechAUTHORS:SHIHcec84
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:56127
Deposited By: Anne Hormann
Deposited On:27 Mar 2015 23:37
Last Modified:10 Nov 2021 20:54

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