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Reactions of polymerization-resistant 1,2-dithiolanes with lithiated oxygen heterocycles

โœ Scribed by Masato Tazaki; Toshihiko Hieda; Hironori Maeda; Shizuo Nagahama; Akinori Jyo

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
185 KB
Volume
9
Category
Article
ISSN
1042-7163

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โœฆ Synopsis

Lithiated furans have been found to cleave the S-S bond of polymerization-resistant 1,2dithiolanes to give the ring opened products in good yields. In the case of lithiated benzofuran, the excess reagent reacted with the normal product to give a mixture. Lithiated dihydrofuran and dihydropyran gave the corresponding ring-opened products that rearranged to spiro-1,3-dithianes during acidic workup. The reaction was applied to the selective synthesis of substrates for intramolecular Diels-Alder reactions.

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