Other nitrating agents

Alkenes react with nitryl chloride to give jS-nitroalkyl chlorides, jS-chloroalkyl nitrites and vic-dichloroalkane products. Nitryl chloride reacts with enol esters to give o -nitroketones.  

A process known as alkene nitrofluorination has been extensively used for the synthesis of /3-nitroalkyl fluorides. Reagents used generate the nitronium cation in the presence of 

A mixture of silver nitrite and iodine reacts with alkenes to give jS-nitroalkyl iodides, and therefore, provides a convenient route to a-nitroalkenes. Treatment of alkenes with ammonium nitrate and trifluoroacetic anhydride in the presence of ammonium bromide, followed by 

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When considering aromatic nitration, it seems reasonable to examine other nitrating agents (besides the nitrating mixture leading to the formation of nitronium ion) and outline the scope of ion-radical mechanism in each case. 

The reaction of alkenes with nitrogen oxides and other nitrating agents have been extensively discussed by Olah, Topchiev, and in numerous reviews." ... 

Acetic anhydride-nitric acid mixtures are extensively used for chloride-catalyzed nitrations. Other nitrating agents have been used and involve similar sources of electropositive chlorine for intermediate chloramine formation. 4,10-Dinitro-4,10-diaza-2,6,8,12-tetraoxaisowurtzitane (TEX) (40), an insensitive high performance explosive (VOD 8665 m/s, d = 1.99 g/cm ), is synthesized by treating the dihydrochloride salt of the corresponding amine (39) with strong mixed acid. ... 

Katritzky and cowoikers have nitrated hydrazinium salts and 1,1-disubstituted hydrazines widi nitio-nium tetrafluoroborate and other nitrating agents. Thus, nitrimides RaN N N02 were prepared in good yield from hydrazinium salts derived from tertiary amines such as trimediylamine and 2-mediylpyiidine ... 

Other nitrating agents which are the source of N02 ion can also be used (Chapter I). 

Other nitrating agents which have been used include dilute nitric acid [245] and copper(II) nitrate in acetic anhydride [298],... 

Nitryl chloride is a selective nitrating agent for the prepn. of compds. such as 1-nitroacenaphthylene or 9-nitrophenanthrene. It is superior to other nitrating agents for this purpose. The reactions are performed in CCI4 at -5 to 5° without catalyst. H. lida, I. Kajiyama, and K. Yamada, Nippon Kagaku Kaishi 1972 (1), 137 (Japan) C. A. 76, 99395. 

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