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Improved synthesis for TNC |
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In 1993, Bashir-Hashemi showed the cubane-1,3,5,7-tetracarboxylic acid chloride can be formed by applying photochemically induced chlorocarbonyl cation( the Kharasch_Brown Reaction). For a fast reaction, a high power Hanovia of 450 watts, medium pressure Hg was used. The favoured products are cubane tetraacid chloride shown on the right hand side. The first one, cubane-1,3,5,7-tetracarboxylic acid, made up 30% overall. This reaction conveniently prepare us the important versatile intermediate . A detail conversion process is provided below: |
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| A catalyst TMSN3 is used in converting tetraacid chloride to tetracylazide. The rest is the same as the orginal reaction. | ||||||||||||||||||||||
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| TNC is a thermodynamic powerhouse but remarkly stable kinetically. Figure 1 shows that rapid thermal decomposition doesnot start until over 250°C. | ||||||||||||||||||||||
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