Accession Number:

AD0904111

Title:

Reactions of Tetrakis(Dimethylamino)Ethylene with Weak Acids.

Descriptive Note:

Technical publication,

Corporate Author:

NAVAL WEAPONS CENTER CHINA LAKE CA

Personal Author(s):

Report Date:

1972-10-01

Pagination or Media Count:

20.0

Abstract:

Tetrakisdimethylaminoethylene reacts in methanol at 25 degrees to give carbon-carbon bond cleavage, substitution of methoxyl for dimethylamino and addition of methanol to the double bond. The principal products are dimethylamine, dimethoxydimethylaminomethane and 1,1,2-trimethoxy-1,2-bisdimethylaminoethane. Minor products are methoxydimethylamino-N,N-dimethylacetamide, trimethylamine and dimethyl ether. An oxidation-reduction side reaction forms a very small amount of the radical cation of tetrakisdimethylaminoethylene. In the presence of sodium methoxide no carbon-carbon bond cleavage occurs and no radical cation is formed. When methanol is dissolved in tetrakisdimethylaminoethylenemethanol 1M, the principal products are 1,1,2-trimethoxy-1,2-bisdimethylaminoethane and dimethylamine with small amounts of trisdimethylaminomethoxyethylene and 1,2-bisdimethylamino-1,2-dimethoxyethylene. Tetrakisdimethylaminoethylene and water give dimethylamine and dimethylformamide. Author

Subject Categories:

  • Organic Chemistry
  • Physical Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE