SYNTHESIS OF MONOHALOCYCLOPROPANES AND 1-HALOOLEFINS VIA PHENYL-(DIHALOMETHYL) MERCURY COMPOUNDS,

Abstract

Previous studies of the synthesis of gem-dihalocyclopropanes using C6H5HgCX2Br compounds as CX2 sources were extended to an investigation of the utility of C6H5HgCHXBr compounds in the preparation of monohalocyclopropanes. It was found that both compounds (X=Cl and Br) serve excellently in the preparation of monohalocyclopropanes. A further similarity of C6H5HgCHXBr reagents to C6H5HgCX2Br compounds is seen in their reactions with triethylsilane. A new, general synthesis of vinylic bromides and chlorides based on (dihalomethyl) mercurial chemistry was developed: C6H5HgCHXBr + (C6H5)3P + RR'C=O yields RR'C=CHX + C6H5HgBr + (C6H5)3PO. This general procedure also is applicable to the preparation of olefins of type RR'C=CX2 from aldehydes and ketones. (Extracted)

Document Details

Document Type
Technical Report
Publication Date
Jan 15, 1965
Accession Number
AD0617596

Entities

People

  • Dietmar Seyferth
  • Gurdial Singh
  • Harry D. Simmons Jr.

Organizations

  • Massachusetts Institute of Technology

Tags

DTIC Thesaurus Topics

  • Aldehydes
  • Chemical Compounds
  • Chemical Synthesis
  • Chemistry
  • Chlorides
  • Elements
  • Group 12 Elements
  • Mercury
  • Mercury Compounds
  • Metals
  • Organic Chemistry
  • Transition Metals

Fields of Study

  • Chemistry

Readers

  • Analytical Mechanics
  • Energy Conservation and Renewable Energy Engineering.
  • Organic Chemistry