90996-81-9Relevant articles and documents
Substituted Thian-4-ones. Part 3. Synthesis and Reactions of 2-Alkyl-5,6-Dihydrothiin-4-ones
Kansal, Vinod K.,Taylor, Richard J. K.
, p. 703 - 708 (2007/10/02)
A number of approaches to the synthesis of 2-alkyl-5,6-dihydrothiin-4-ones (1) are described.The treatment of 2-butylthian-4-one (3) with N-chlorosuccinimide gave a mixture of the alkenes (1a) and (4) and the corresponding reaction with the dioxolane (5) also proved to be non-regioselective. 2-Chlorodihydrothiin-4-one (6) was prepared and its reactions with a number of butylcoper reagents studied.The only product isolated from these reactions was 2,2-dibutylthian-4-one (12). 3-Chlorodihydrothiin-4-one (8) was successfully prepared and converted into 2-butyl-3-chlorothian-4-one (13) but dehydrohalogenation could not be achieved.A successful synthesis of the title compounds was achieved based on the generation and alkylation of the β-acylvinyl anion equivalent (14).Attempts to desulphurise 2-benzyl-5,6-dihydrothiin-4-one (1d) and related compounds in order to produce the α,β-unsaturated ketone (18) are discussed.
