Accession Number:

ADA251352

Title:

Exchange Reactions of Organotin and Organosilicon Compounds with Mild Fluorinating Agents

Descriptive Note:

Final rept. Sep 1986-Oct 1988,

Corporate Author:

CHEMICAL RESEARCH DEVELOPMENT AND ENGINEERING CENTER ABERDEEN PROVING GROUND MD

Personal Author(s):

• Rossman, David I.
• Muller, August J.

Report Date:

1992-03-01

Pagination or Media Count:

19.0

Abstract:

A diverse group of compounds bearing labile fluorine atoms have been found to undergo similar exchange reactions with various organosilanes and stannanes. For example, methylphosphonic difluoride, boron trifluoride etherate, and perfluoroisobutene all react with both organosilicon and organotin alkoxides to give products resulting from the exchange of fluoride for an alkoxide group. In contrast to reactions involving the use of protic nucleophiles that may yield these products, hydrogen fluoride is not formed as a byproduct in these systems. Organotin compounds have been found to be more reactive than their silicon based analogs. Mechanisms are proposed to account for the products and the reactivity differences observed in these systems. These reactions have proven useful for the routine synthesis of various compounds.

Descriptors:

• *EXCHANGE REACTIONS
• *FLUORINATED HYDROCARBONS
• REACTIVITIES
• ATOMS
• HYDROGEN
• FLUORINE
• SILICON
• YIELD
• ADDITION
• BEARINGS
• ESTERS
• BORON
• ELIMINATION
• FLUORIDES
• EXCHANGE
• HYDROGEN FLUORIDE
• SYNTHESIS
• CONTRAST
• ANALOGS

Subject Categories:

• Inorganic Chemistry
• Organic Chemistry
• Atomic and Molecular Physics and Spectroscopy

Distribution Statement:

APPROVED FOR PUBLIC RELEASE