chapter  2
18 Pages

HIGH-ENERGY, HIGH-DENSITY, POLYCYCLIC HYDROCARBONS AND AZIDO DERIVATIVES

The primary objective of this research was the synthesis of cubane analogs

which contained polyunsaturated side-chains, which, in turn, could be used as

starting materials for the production of high-energy derivatives [1{5]. Target

molecules were 1,4-bis-azidomethyl cubane, 1,4-bis(1

,2

-diazidomethyl)cubane,

1,4-bis(2

,3

-diazidopropyl)cubane, 1,4-bis(2

,3

-diazidopentyl)cubane, 1

,4

-

bis(2

,3

-diazidohexyl)cubane, and 1,4-bis(2

,3

-diazidoheptyl)cubane. The ra-

tionale for the design of these analogs is centered around the combination of

two energetic groups, namely, the azido group and the cubane system within the

same molecule. The thermal decomposition of alkyl azides proceeds with loss of

molecular dinitrogen and production of an alkyl nitrene:

-

RCH

{N

[RCH

{N] + N

@

@R

RCH=NH RN=CH

This process has been shown in collaboration with C.K. Law of Prince-

166 kcal/mole and ring opening releases a substantial amount of this strain en-

ergy.