1,2-Dicyclopropylethyne and (Cyclopropylethynyl)cyclobutane from an Efficient Synthesis of 1,2-(omega-Haloalkyl)ethynes and 1-Cycloalkyl-2-(omega-haloalkyl)ethynes (Pre Print)

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 Bu4NI at 70 degrees C to furnish omega-haloalkyl acetylenes in very good yields. The omega-haloalkyl acetylenes undergo intramolecular alkylation with LDA to provide dicycloalkyl-ethynes.

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Document Details

Document Type
Technical Report
Publication Date
Feb 09, 2012
Accession Number
ADA613652

Entities

People

  • Jacob C. Marcischak
  • Suresh C. Suri

Organizations

  • Air Force Research Laboratory

Tags

Communities of Interest

  • Weapons Technologies

DTIC Thesaurus Topics

  • Acetylenes
  • Air Force
  • Air Force Research Laboratories
  • Alkanes
  • Alkylation
  • Alkynes
  • Chlorides
  • Cyclic Hydrocarbons
  • Cyclobutanes
  • Distillation
  • High Temperature
  • Low Temperature
  • Metals
  • Military Research
  • Mixtures
  • Pyridines
  • Terminals

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry