Dinitro compounds, olefins from

In the past the products from the addition of dinitrogen totroxide to olefins have been hydrolyzed and then converted to 1-nitro olefins by various methods, e.g., acetylation of the isolated nitro alcohol and elimination of acetic acid with potassium carbonate,5 6 dehydration of the nitro alcohol with phthalic anhydride7 or potassium hydrogen sulfate,8 and base-catalyzed elimination of nitrous and nitric acid from dinitro compounds and nitro nitrates, respectively.2 Besides representing longer syntheses, these routes require separation of the... 

Olefin synthesh. Komblum ei a . have described a new synthesis of tetrasubsti-tuted olefins from vicinal dinitro compounds. There are several methods for conversion of aliphatic and alicyclic nitro compounds into nic-dinitro compounds, the most useful of which is a procedure of Seigle and Hass. A nitroparafhn is converted into (he lithium salt (I) by treatment with lithium methoxidc and this is then treated with bromine to form a bromonilro compound (2). Reaction of (2) with a second equivalent of the nitro-R.. NO,, ... 

Aliphatic dinitro compounds, nitronitric acid esters, and nitroalcohols from olefins... 

This reaction was improved by sonication in the case of lipidic substrates. The reductive elimination of i /c-dinitro compounds to olefins, usually effected with tributyltin hydride, was achieved successfully by nickel boride (prepared from nickel chloride and sodium borohydride by sonication in methanol for 30 min) giving olefins in excellent yields (Eq. 37). The reagent is prepared by sonication of nickel chloride and sodium borohydride and gives the so-called nickel boride. 

Primary alkyl phenyl tellurides undergo elimination to form terminal olefins in high yields on treatment with an excess of iV-chloro-iV-sodio-4-methyl-benzenesulphonamide (chloramine-T) in refluxing THF/ ufc-Dinitro compounds and /3-nitrosulphones are converted into olefins via free-radical elimination processes on treatment with tributyltin hydride in the presence of catalytic quantities of azobis(isobutyronitrile) (AIBN). Elimination from the dinitro compounds shows no stereocontrol by contrast, elimination from /3-nitrosulphones is highly stereoselective, e.g. (26)- (27), presumably because elimination from the intermediate radical is faster than rotation about the central carbon-carbon bond. 

The main index headings for search other than the names of specific compounds are Paraffins nitration of Paraffins, nitro Paraffins, from nitration of— Paraffins, dinitro Hydrocaibons, nitration of Nitration of hydrocarbons Nitration of paraffins Petroleum, nitrogen compounds from Olefins, nitro derivatives and Acetylenes, nitro derivatives. These items are not mutually inclusive, e.g., references under Paraffins, nitration of are not necessarily to be found under Nitration of paraffins. In Chemical Abstracts collective index for 1937 to 1946, there are 19 entries under the first heading and 12 entries under the second only 10 are common to both lists. 

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