35520-82-2

Upstream product

• 2534-77-2 exo-2-bromonorbornane 
• 74087-85-7 3,3-dimethyldioxirane 
• 65481-69-8 bicyclo[2.2.1]heptan-2-endo-amine hydrochloride 
• 874-44-2 5-endo-nitrobicyclo<2.2.1>hept-2-ene 
• 64-19-7 acetic acid 
• 279-23-2 norbornene 
• 6343-65-3 endo-2-nitronorbornane 
• 7242-92-4 exo-2-aminonorbornane 

Downstream Products

• 497-38-1 Norbornan-2-on 
• 4576-48-1 2-norbornanone oxime 
• 74221-99-1 N-hydroxy-3-azabicyclo<3.2.1>octan-2-one 
• 74222-01-8 N-hydroxy-2-azabicyclo<3.2.1>octan-3-one 
• 97945-32-9 2-Bicyclo[2.2.1]hept-(2Z)-ylidenemethyl-1-methyl-5-nitro-1H-imidazole 
• 497-38-1 2-norbornanone 
• 6343-65-3 exo-2-nitronorbornane 
• 7242-92-4 exo-2-aminonorbornane 
• 3281-03-6 norcamphor 2,4-dinitrophenylhydrazone 
• 158506-27-5 endo-2-Nitro-2-fluoronorbornane 
• 158506-27-5 exo-2-Nitro-2-fluoronorbornane 
• 97945-32-9 (E)-1-methyl 2-(2-norbornanylidenemethyl) 5-nitroimidazole 

Relevant academic research and scientific papers

SRN1 reactions in the nitrobenzo[1,3]dioxole series

5-Chloromethyl-6-nitrobenzo[1,3]dioxole has been shown to react with 2-nitropropane anion to give C-alkylation by an SRN1 mechanism. The reaction was extended to various aliphatic, cyclic, and heterocyclic nitronate anions, leading to a new series of nitrobenzo[1,3]dioxole derivatives.

Oxygenation of Bicycloheptane and Bicyclooctane with Nitronium Tetrafluoroborate

Reaction of bicycloheptane (1) with nitronium tetrafluoroborate in nitroethane gives bicycloheptan-2-one (2).Bicycloheptan-2-yl nitrite (3) was observed as the intermediate of the reaction.The reaction of exo-bicycloheptan-2-ol (4) with nitrosonium tetrafluoroborate also gave 2.The reaction of 2-norbornyl cation with silver nitrite gave 2.When exo-2-bromobicycloheptane (10) reacted with silver nitrite in ether, 2 and 2-nitrobicycloheptan (8) were obtained in 1.3:1 ratio.Reaction of bicyclooctane (5) with nitronium tetrafluoroborate yields upon aqueous workup bicyclooctan-1-ol (6).No nitro products were observed in either of the reactions.The mechanism of the observed reactions is discussed.

Fluorination of Nitro Compounds with Acetyl Hypofluorite

Various types of nitro derivatives are fluorinated to form the CFNO2 moiety in very good yields using acetyl hypofluorite (AcOF).The corresponding nitro anion, preferably prepared with NaOMe, is added quickly to a cold (-75 deg C) CFCl3 solution of AcOF,

S(RN)1 synthesis of new 5-nitroimidazoles highly active against protozoa and anaerobes

1-Methyl-2-chloromethyl-5-nitroimidazole reacts by an S(RN)1 mechanism with various aliphatic, cyclic or heterocyclic nitronate anions to afford, in high yields, new 5-nitroimidazoles bearing a trisubstituted ethylenic double bond at the 2 position. Some of these compounds are as active as metronidazole in vitro and in vivo against protozoa and anaerobic bacteria. Structure-activity relationships are discussed.

Synthesis by the S(RN)1 reaction of a new series of imidazo[1,2-a]pyridine derivatives with pharmacological potentialities

The study of S(RN)1 reaction between 2-chloromethyl-3-nitroimidazo[1,2-a] pyridine and 2-nitropropane salts has been extended to various aliphatic, cyclic and heterocyclic nitronate anions. From C-alkylation products, base-promoted nitrous acid elimination afforded new potential pharmacological derivatives with a trisubstituted double bond at the 2 position.

Oxidation of Primary Amines by Dimethyldioxirane

Dimethyldioxirane oxidizes primary amines rapidly, and generally in high yield, to the corresponding nitro compounds.The method can also be used to syntesize polynitro compounds.