Mechanism and stereochemistry of domino reaction of 2,3-dichloroprop-1-ene with diphenyl dichalcogenides in the system hydrazine hydrate-KOH

作者：Levanova E P^*; Vakhrina V S; Grabel'nykh V A; Rozentsveig I B; Russavskaya N V; Albanov A I; Korchevin N A

来源：Russian Chemical Bulletin, 2015, 63(8): 1722-1727.

DOI：10.1007/s11172-014-0659-7

• domino reactions
• 2,3-dichloroprop-1-ene
• chalcogen-containing nucleophiles
• stable carbanions
• hydrazine hydrate
• stabilization
• stereochemistry
• mechanism

A new scheme of the domino reactions of diphenyl dichalcogenides with 2,3-dichloroprop-1-ene in the system hydrazine hydrate-KOH was suggested, which included nucleophilic substitution of the allylic chlorine atom in dichloropropene, dehydrochlorination of the product obtained with the formation of an allene derivative, addition of a nucleophile to the allene system, allene-acetylene rearrangement, addition of a nucleophile to the triple bond with the formation of a Z-adduct, isomerization of a 2,3-dichalcogenide product to Z-1,2-dichalcogenylprop-1-enes, and isomerization of Z-adducts to E-isomers. The most plausible mechanisms of individual steps, involving carbanions stabilized by the alpha-chalcogen atom, were considered.

• 出版日期2015-8