R. Aitken
1990
Citations
0
Influential Citations
4
Citations
Journal
Progress in Heterocyclic Chemistry
Abstract
Publisher Summary This chapter presents the syntheses and reactions of five-membered heterocyclic ring systems containing oxygen and sulfur (or selenium, tellurium), particularly of dioxolanes and oxathiolanes. Hydroxyacetophenones are conveniently converted into the corresponding 1,3- dioxolanes by treatment with ethanediol and tri-isopropyl orthoformate in the presence of catalytic cerium triflate, and the reaction of ketones with PhICl 2 and ethanediol gives the a-chloro-1,3-dioxolanes. New theoretical studies have appeared on 2-methylene-1,3-dioxolane, 1,3-dioxol-2-one, and 1,3-dioxole-2-thione and on their radical cations. Newly reported X-ray structures of 1,3-dioxolanes include the series of diamides that are important intermediates in the synthesis of anti-cancer platinum drugs, the dioxolodioxasilepine, which is a chiral dopant for liquid crystals, the chiral diphosphine ligand, and the bis(spiro) biphenyl. The reaction of carbonyl compounds with ethanedithiol to give 2-substituted 1,3-dithiolanes can be achieved under solvent-free conditions using either the ionic liquid Et 3 N + (CH 2 ) 4 SO 3 H TsO – or P 2 O 5 /Al 2 O 3 and microwave irradiation.