Accession Number:

ADA199472

Title:

Synthesis of Energetic Materials

Descriptive Note:

Annual Progress rept. 1 Jan-31 Dec 1987

Corporate Author:

NAVAL SURFACE WARFARE CENTER SILVER SPRING MD

Personal Author(s):

Report Date:

1988-03-01

Pagination or Media Count:

19.0

Abstract:

Salts of ethylenedinitramine EDNA and methylenedinitramine MEDINA reacted successfully with 4, 5-dichloro-1, 3-dioxalan-2-one to yield bicyclic carbonate esters, which underwent ester cleavage with boron tribromide to give 2, 3-dibromo-1, 4-dinitropyrazine and 4, 5-dibromo-1, 3-dinitroimidazolidine respectively. Attempts to convert the latter dibromide into bicyclo-HMX by reaction with salts of MEDINA were unsuccessful, probably as a result of debromination leading to an unstable olefinic cyclic dinitramine. U The cyclic dinitramine derivative, 2, 3-diacetoxy-1, 4-dinitropyrazine reacted with excess ethyl urethane, under boron trifluoride catalysis in trifluoroacetic acid, to give the 2, 3-bisurethane derivative. This conversion represents the first successful attempt to introduce nitrogen functionality adjacent to a nitramino group to form an animal-type linkage. Similarly, the diacetoxy pyrazine reacted with urea to give a bicyclic urea derivative, which was nitrated with nitric acid-acetic anhydride to yield the tetranitro-tetraazabicyclononanone. Nitramines Esters Chlorine compounds Cyclic compounds Energetic materials.

Subject Categories:

  • Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE