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Nucleophilic substitution reactions of thienyl neopentyl substrates

McLure, F.I., Norris, R.K. and Wilson, K. (1987) Nucleophilic substitution reactions of thienyl neopentyl substrates. Australian Journal of Chemistry, 40 (1). pp. 49-60.

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The reaction of the chlorides (4)-(6), which are both neopentylic and thenylic , were studied. The chloride (4), unlike its analogue (13) in the benzene series, undergoes ready solvolysis with alcohols to give the corresponding ethers, e.g. (7)-(9). The chlorides (5) and (6) react more slowly than (4) but undergo methanolysis to give the methyl ethers (11) and (12) respectively. In the dipolar aprotic solvents, dimethyl sulfoxide and dimethylformamide, the reactions of the chlorides (4), (5) and (6) with the thiolate salt (16) appear to proceed by an SN1-like, an SN(AEAE) and an SRNl process respectively.

Item Type: Journal Article
Publisher: Commonwealth Scientific and Industrial Research Organization Publishing
Copyright: © 1987 CSIRO
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