Nucleophilic Substitution Reactions of Thienyl Neopentyl Substrates

Felicity I. McLure, Robert K. Norris, Karen Wilson

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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 SRN1 process respectively.

Original languageEnglish
Pages (from-to)49-60
Number of pages12
JournalAustralian Journal of Chemistry
Issue number1
Publication statusPublished - 1987
Externally publishedYes


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