An Efficient Synthesis of Dicycloalkylacetylenes: 1,2-Dicyclopropylethyne and (cyclopropylethynyl)cyclobutane (Preprint)

Abstract

Lithium acetylides, generated from terminal acetylenes with n-BuLi in THF at -70 degrees C, react chemoselectively with omega-haloalkyl tosylate in the presence of 10 mole % of Bu4I at 70 degrees C to furnish omega-haloalkyl acetylenes in very good yields. The omega-haloalkyl acetylenes were subject to intra-molecular alkylation with LDA to provide dicycloalkylethyne.

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Document Details

Document Type
Technical Report
Publication Date
Nov 05, 2008
Accession Number
ADA503213

Entities

People

  • Jacob C. Marcischak
  • Suresh C. Suri

Organizations

  • Air Force Research Laboratory

Tags

Communities of Interest

  • Biomedical

DTIC Thesaurus Topics

  • Acetylenes
  • Air Force
  • Air Force Research Laboratories
  • Alkanes
  • Alkylation
  • Alkynes
  • Chemical Compounds
  • Chemical Synthesis
  • Chemistry
  • Cyclic Hydrocarbons
  • Cyclobutanes
  • Cyclopropanes
  • Materials
  • Military Research
  • Organic Chemistry
  • Terminals

Fields of Study

  • Chemistry

Readers

  • Government and Public Administration Law.
  • Materials Science.
  • Polymer Science and Technology