Preparation and Reactivity of Mixed Benzylic 1, 1 -Dimetalloalkanes

Paul Knochei*, Ming Chang P. Yeh, Chaodong Xiao

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)


The carbometalation of (α-styryl)magnesium or -lithium organometallics with various allylic zinc bromides allows a general preparation of mixed benzylic 1, 1-dimetalloalkanes in good to excellent yields. Their low reactivity can be increased by a transmetalation with copper cyanide leading to copper, zinc dimetallic reagents which are readily bis-allylated with allyl bromide or bis-stannylated with trimethyltin chloride. Transmetalation with 1 equiv of trimethyltin chloride in the absence of copper salts affords tin, zinc 1, 1-dimetallo derivatives that can be cleanly oxidized by air to aromatic ketones under very mild conditions (-10 to 0 °C, 0.5-4 h). The monolithiation of the bis(trimethylstannyl) derivative 7 provides the a-lithiated benzylic tin compound 8 whose reactivity is also described.

Original languageEnglish
Pages (from-to)2831-2835
Number of pages5
Issue number12
Publication statusPublished - 1989 Dec
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry


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