136476-37-4

Upstream product

• 39590-81-3 [1-(hydroxymethyl)cyclopropyl]methanol 
• 136476-33-0 1-Azidomethyl-1-nitromethyl-cyclopropane 
• 136476-42-1 cis-1,2-diiodo-1,2-dinitrospiropentane 
• 136476-43-2 (1S,2S)-1,2-Diiodo-1,2-dinitro-spiro[2.2]pentane 
• 38932-70-6 C-(1-Aminomethyl-cyclopropyl)-methylamine 
• 136476-38-5 cyclopropane-1,1-diylbis(methylene) dimethanesulfonate 
• 136476-39-6 1,1-bis(azidomethyl)cyclopropane 
• 598-10-7 cyclopropane-1,1-dicarboxylic acid 
• 100-52-7 benzaldehyde 
• 136476-35-2 trans-1,2-dinitrospiropentane 
• 136476-32-9 1,1-bis(nitromethyl)cyclopropane 

Relevant academic research and scientific papers

Polynitro-substituted strained-ring compounds. 2. 1,2-Dinitrospiropentanes

trans-1,2-Dinitrospiropentane was prepared in 43% yield from 1,1-bis(nitromethyl)cyclopropane, best obtained by dry-phase ozonolysis of the corresponding diamine. The structure of trans-1,2-dinitrospiropentane was assigned on the basis of spectroscopic data, elemental analysis, and X-ray crystallographic data. The first pKa was determined to be 18.6-21.6 in DMSO solution with decomposition. Reaction of trans-1,2-dinitrospiropentane with sodium methoxide and iodine gave a mixture of iodinated spiropentanes, from which, cis- and trans-1,2-diiodo 1,2-dinitrospiropentane could be isolated in pure form. These diiodides were stable at room temperature but gave off iodine upon melting at 150-160°C. Treatment with sodium thiosulfate in aqueous DMSO solution gave back the deiodinated dinitro compound. trans-1,2-Dinitrospiropentane reacted with lithium diisopropylamide and benzaldehyde in THF to afford a bis(nitroaldol) product in 59% yield.