The Journal of Organic Chemistry

Synthesis of 5, 5, 9, 9-tetranitropentacyclo [5.3. 0.02, 6.03, 10.04, 8] decane

AP Marchand, DS Reddy

Index: Marchand, Alan P.; Reddy, Sivakumar D. Journal of Organic Chemistry, 1984 , vol. 49, # 21 p. 4078 - 4080

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Citation Number: 27

Abstract

Pentacyclo [5.3. 0.~.~ 10.0@] decane-5, 9-dione (7). Compound 7 was synthesized by the following reaction sequence: 1, 4-dioxaspiro [4.4] nonane, 2, bp 152-155 OC (lit. bp 153 OC)'O was syntheaized in 90% yield via reaction of cyclopentanone with ethylene glycol in the presence of p-toluenesulfonic acid (benzene solvent).'O Bromination of 2 with bromine (2 equiv) in dry dioxane at 10-15 OCll afforded the corresponding dibromide 3 (55%), mp ...