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Selenosulfonation of acetylenes. Preparation of novel β-(phenylseleno)vinyl sulfones

✍ Scribed by Thomas G. Back; Scott Collins

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
160 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

Se-Phenyl p-tolueneselenosulfonate (1) undergoes thermal addition to acetylenes to afford P-(phenylseleno)vinyl sulfone adducts 2 in a stereo-and regioselective fashion. -We recently reported that Se-phenyl areneselenosulfonates (e.g. 1) add to olefins on heating or at room temperature in the presence of boron trifluoride etherate to give P-2 (phenylseleno) sulfones . Lewis acid-catalyzed additions of 1 to olefins proceed with pre-dominantly Markovnikoff orientation and are stereospecifically anti. An electrophilic addition mechanism involving bridged seleniranium ions has been proposed 2b . In contrast, ther- mally initiated additions of 1 afford adducts of opposite regiochemistry and are nonstereospecific. A free radical addition mechanism has been implicated in this case 2b,3 . We now report that 1 adds to acetylenes under thermal conditions to afford P-(phenylselenojvinyl sulfones 2 4-(eqn. 1). _ eqn. 1 ArSO*SePh + R-CIC-R' 2 R\ ,SePh ,c=c\

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