Preparation and Reactivity of Mixed Benzylic 1, 1 -Dimetalloalkanes

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

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

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
JournalOrganometallics
Volume8
Issue number12
DOIs
Publication statusPublished - 1989 Jan 1
Externally publishedYes

Fingerprint

Copper
reactivity
zinc
copper
preparation
Zinc
bromides
Tin Compounds
chlorides
tin compounds
Derivatives
Tin
Cyanides
cyanides
Organometallics
Ketones
Lithium
ketones
Magnesium
reagents

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Preparation and Reactivity of Mixed Benzylic 1, 1 -Dimetalloalkanes. / Knochei, Paul; Yeh, Ming-Chang P.; Xiao, Chaodong.

In: Organometallics, Vol. 8, No. 12, 01.01.1989, p. 2831-2835.

Research output: Contribution to journalArticle

Knochei, Paul ; Yeh, Ming-Chang P. ; Xiao, Chaodong. / Preparation and Reactivity of Mixed Benzylic 1, 1 -Dimetalloalkanes. In: Organometallics. 1989 ; Vol. 8, No. 12. pp. 2831-2835.
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