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Abstract Mnogo lishnego!

 

 

Readily available Tricyclooctadiene 1 was prepared from dicyclopropylethyne in two steps stages. In first operation was obtained adduct syn-2 in 67% yield, witch solution in pentane upon irradiation was entered involved an intramolecular [2+2] cycloaddition to give octacyclopropylcubane (3) in 48% yield. This new cubane derivative have very high overall strain energy (ca., 390 kcal mol–1), also it have specific physical and chemical properties.

Abstract Mnogo lishnego!

 

Successful methodology for the synthesis of highly nitrated cubanes was developed. Four of the eight nitro groups of octanitrocubane 1 are introduced by dimethyldioxirane oxidation of the

tetraamine derived from Curtius-type transformations of the corresponding tetraacid; three more by the astonishingly rapid, low-temperature N2O4 nitration of sequentially formed polynitrocubyl anions via 4 equiv of NaN(TMS)2 at -78.8°C; and last by addition of excess nitrosyl chloride to a solution of the lithium salt of heptanitrocubane (from 4 and LiN(TMS)2) in CH2Cl2 at -78.8°C followed by ozonation. Application of the Kamlett-Jacobs equations to octanitrocubane leads to calculated detonation velocities and pressures much higher than classic C-nitro explosive TNT, N-nitro compound HMX, and polycyclic nitramine CL-20.


Date: 2014-12-22; view: 1015


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