Reaction of Chlorosulfonyl Isocyanate (CSI) with Fluorosubstituted Alkenes: Evidence of a Concerted Pathway for Reaction of CSI with Fluorosubstituted Alkenes (Preprint)

Abstract

Concerted reactions are indicated for the electrophilic addition of chlorosulfonyl isocyanate with monofluoroalkenes. A vinyl fluorine atom on an alkene raises the energy of a step-wise transition state more than the energy of the competing concerted pathway. This energy shift induces CSI to react with monofluoroalkenes by a one-step process. The low reactivity of CSI with monofluoroalkenes, stereospecific reactions, the absence of 2:1 uracil products with neat fluoroalkenes and quantum chemical calculations support a concerted pathway.

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Document Details

Document Type
Technical Report
Publication Date
Jun 01, 2010
Accession Number
ADA523002

Entities

People

  • Arnold L. Reingold
  • Chris E. Moore
  • Dale Shellhamer
  • Danielle M. Hassler
  • David J. Vandenbroek
  • Jacob J. Thorpe
  • Jerry A. Boatz
  • Kelli R. Hickle
  • Kevyn J. Davenport
  • Victor L. Heasley

Organizations

  • Air Force Research Laboratory

Tags

Communities of Interest

  • Advanced Electronics
  • C4I
  • Energy and Power Technologies
  • Materials and Manufacturing Processes

DTIC Thesaurus Topics

  • Air Force
  • Air Force Research Laboratories
  • Alkenes
  • Cartesian Coordinates
  • Chemical Compounds
  • Chemical Synthesis
  • Chemistry
  • Chlorides
  • Chromatography
  • Column Chromatography
  • Fluorine
  • Isocyanates
  • Organic Chemistry
  • Sulfur Compounds
  • Transitions

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry
  • Quantum Chemistry

Technology Areas

  • Quantum Computing