Synthese de sulfites cycliques a groupe SO equatorial

Synthesis of sultines via tert-butyl hydroxyalkyl sulfoxides

“…Isomerization, possibly acid catalyzed, of the various isomers may be sufficiently facile so that our isolation procedures produced only the most stable one. Both sulfites (15) and sulfoxides (16) have been shown to undergo acid-catalyzed epimerization.…”

Synthesis of 1,2-annulated adamantane heterocycles: structural determination studies of a bioactive cyclic sulfite

“…The novel heterocycle 3-oxatetracyclo[5.3.1.1 5,9 .0 2,5 ]dodecane 4 is prepared by a simple and effective method, involving synthesis of the corresponding 2-hydroxy-1-adamantanomethanol followed by its intramolecular cyclization with thionyl chloride, along with 4-oxo-adamantane-3,5,4-dioxathiane 5 in yields depending on the reaction temperature. Dioxathiane 5 was markedly active against vesicular stomatitis virus, its potency being 2.5-fold higher than that of (S)-9-(2,3-dihydroxypropyl)adenine.…”

“…Among 2-oxo-1,2,3-dioxathiane structures, the cyclic sulfite analogues of topiramate have proven to be promising anticonvulsant agents, 1h whereas a cyclosulfite podophyllotoxin analogue was shown to be a potent antitumor agent. 1i Moreover, the conformation of 2-oxo-1,3,2-dioxathianes has been studied intensively by means of dipole moments, 3 infrared spectroscopy, 4,5 electron diffraction, 6 chemical equilibration, 7 ultrasonic absorption, 8 1 H and 13 C NMR spectroscopy, 4,5,[9][10][11] X-ray diffraction, 12 and mass spectroscopy. 13 It has been shown that an equilibrium exists in this type of rings with the exocyclic oxygen in the axial or equatorial orientation depending on the substituents of the six-membered ring.…”