Sultones reduction

Thiophenes can be prepared from the sultones of a,j8-unsaturated ketones. From the 8-sultone of pulegone (89), the thiophene (91) has been obtained through reduction with LiAlHi to (90), followed by dehydration of the latter. ... 

Sultines can be versatile synthetic intermediates for example, they undergo ring-opening reactions, alkylation, reductive desulfurization , and oxidation at sulfur to give sultones. 

A more detailed examination of the reduction of bicyclo[2,2,l]heptane sultones [e.g. (185)] with lithium aluminium hydride reveals the formation of the corresponding sulphinates, hydroxy-mercaptans, and sulphur-free alcohols progressively, with... 

A different approach to the asymmetric Diels-Alder reaction involves the use of the sultam derived from CSA. Lewis acid-promoted reaction with dienes followed by reductive removal of the chiral auxiliary is analogous to that previously discussed for the sultone. Smith has successfully utilized this approach to synthesize the chiral acid used in the synthesis of the immunosuppressant FK-506 (eq 16). ... 

Various aluminum hydrides have been found to induce the reductive ring opening of [2.2.1] and [3.2.1] oxabicydic compounds. Metz found that the treatment of sultone 258 with Red-Al resulted in the overall net SN2 addition of hydride and ring opening [165]. When 260 was found to also give 261 under the same reaction conditions, the mechanism postulated to account for this transformation was an initial deprotonation of the sultone 258 by Red-Al and ring opening, followed by the 1,6-delivery of hydride via aluminate 259, and stereoselective protonation, Eq. 162. 

Scheme 10-24 A reductive cleavage strategy has been used to remove the sultone tether.

Besides the above-described polymerizable monomer additives, snlfnr-based componnds were proposed in our group as additives for forming anode SEI, inclnding butyl sultone (BS) [82, 83], propane sultone (PS) [84, 85], prop-l-ene-l,3-sulton (PES) [86], as well as ES [54,87], These sulfur family additives have higher reduction potentials than the electrolyte solvents, as shown in Fig. 5.29. 

The reduction of a number of sultones in the bornyl and camphene series with lithium aluminium hydride can lead to a variety of products, depending on the reaction conditions. Thus 10-isobornyl sultone, when reduced in ether at room temperature, gives the corresponding sultine in 70% yield, whereas reduction in refluxing THF afforded l-mercaptomethyl-2-exo-hydroxy-7,7-dimethyl-bicyclo-[2,2,1 ]heptane. The propargylic sulphite (106), when heated to 180 °C, gave sultone (107) in 22% yield its structure was proved by A"-ray studies. The... 

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