Accession Number:

ADA207869

Title:

Synthesis of 4,4,8,8,11,11-Hexanitropentacyclo(5.4.0.0(2,6).0(3,10).0(5, 9)-undecane

Descriptive Note:

Corporate Author:

NORTH TEXAS STATE UNIV DENTON DEPT OF CHEMISTRY

Report Date:

1989-04-18

Pagination or Media Count:

4.0

Abstract:

The synthesis of the title compound 1 has been accomplished in seven steps by starting with the readily available 4,4,11,11-bisethylenedioxy pentacyclo5.4.0.02,6.03,10.05,9-undecane-9-one 2. Thus, 2 was converted into the corresponding oxime, 3 79. The oximino group in 3 then was subjected to oxidative bromination with N-bromosuccinimide, thereby affording the corresponding exo-8-nitro derivative, 4 62. Sodium borohydride reduction of the C-Br bond in 4 afforded 5 84, which was converted subsequently into the corresponding 8,8-dinitro derivative, 6 83. Acid promoted hydrolysis of the ethylene ketal moiety in 6 afforded 7 50, which was converted subsequently into the corresponding dinitrodioxime, 8 75. Oxidative nitration of 8 afforded 1 19. The structure of 1 was established unequivocally by single crystal X-ray structural analysis. Keywords Hexanitropentacycloundecane Synthesis chemistry X ray structure Cyclic compounds Decanes Hexanes Reprints.

Subject Categories:

  • Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE