A. P. Marchand, P. Dave, D. Rajapaksa
Mar 1, 1989
Citations
0
Influential Citations
14
Citations
Journal
Journal of Organic Chemistry
Abstract
Abstract : The synthesis of the title compound (1) has been accomplished in seven steps by starting with the readily available 4,4,11,11-bis(ethylenedioxy) pentacyclo(5.4.0.02,6.03,10.05,9)-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.