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SN2′ Substitutions of 1,3-Dichloropropenes with the Functionalized Copper-Zinc Reagents RCu(CN)ZnX

✍ Scribed by Gu Chen Huai; Jennifer L. Gage; Stephen D. Barrett; Paul Knochel

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
226 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

The addition of benzenesulfenyl (or benzeneselenyl) chlorides to propargylic chlorides affords regio-and stereospecifically (E)-l,3-dichloro-2-phenylsulfenyl (or phenylselenyl) propenes (2a-c). These new reagents were found to react with excellent SN2" selectivity with the highly functionalized copper-zinc reagents RCu(CN)ZnX, affording polyfunctional vinylic-thioethers or -selenides of type 3. The acidic hydrolysis of 3 furnishes symmetrical ketones in good yields.

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