O Nitrobenzyl chloride

Dicbloronitrobenzene o-Nitrobenzyl chloride m-Nitrobenzyl chloride p-Nitrobenzyl chloride o-Nitrobenzyl bromide m-Nitrobenzyl bromide p-Nitrobenzyl bromide o-Nitrobenzyl iodide m-Nitrobenzyl iodide p-Nitrobenzyl iodide o-Nitrobenzyl cyanide... 

A variation of the Madelung cyclization involves installing a functional group at the o-methyl group which can facilitate cyclization. For example, a triphenylphosphonio substituent converts the reaction into an intramolecular Wittig condensation. The required phosphonium salts can be prepared by starting with o-nitrobenzyl chloride or bromide[9]. The method has been applied to preparation of 2-alkyl and 2-arylindoles as well as to several 2-alkenylindoles. Tabic 3.2 provides examples. 

The American authors suggested (X) or (XI), already considered by Spath and Nikawitz for vasicine, and support for a formula of type (XI) was provided by Spath, Kuffner and Platzer, who, by condensing o-nitrobenzyl chloride with methyl y-aminobutyrate to o-nitrobenzyl-pyrrolidone (XII), reduction of this to the amino-compound (XII NOa —> NHj) and ring-closure in presence of phosphoryl chloride obtained the base d -pegene (XIII), m.p. 99-100°, identical with the product formed by the reduction of deoxychloropeganine. The same substance... 

Nitrobenzyl chlorides are also reduced by microsomes through one-electron reduction mechanism. Moreno et al. [47] suggested that p- and o-nitrobenzyl chlorides are reduced by rat hepatic microsomes to unstable radical anions, which are decomposed to form benzyl radicals under anaerobic conditions. However, in the presence of dioxygen the radical anions of these compounds participate in futile redox cycling yielding superoxide (Figure 24.2). In contrast to p- and o-nitrobenzyl chlorides, m-nitrobenzyl chloride was reduced by microsomes to a relatively stable m-nitrobenzyl radical anion. 

The starting material is prepared as follows the mixture of 54.0 g of N-potassium phthalimide, 50.0 g of o-nitrobenzyl chloride and 120 ml of dimethylformamide is refluxed for 3 hours and poured into 900 ml of ice-water while stirring. After 30 minutes, it is filtered, and the residue washed with water, to yield the N-o-nitrobenzyl-phthalimide melting at 190°-209°C. 

A new synthesis of aporphines has appeared. The key step in this synthesis involves the generation of l-(o-nitrobenzyl)isoquinoline by reaction of a Reissert compound with o-nitrobenzyl chloride in dimethylformamide in the presence of sodium hydride. 

Benzyl iodide o-Nitrobenzyl chloride Dichloromethyl ether Dibromomethyl ether... 

The action of fuming nitric acid introduces a nitro-group into the benzene nucleus and o-nitrobenzyl chloride is formed ... 

French term for mixture of o-nitrobenzyl chloride and / -nitrobcnzyl chloride qv. 

A facile synthesis of d,/-vasicine (33 R = H) has been reported.29 Condensation of o-nitrobenzyl chloride with 3-hydroxypyrrolidine gave compound (52). Reduction of the nitro-function (conditions not given) followed by treatment with mercuric acetate-edta gave vasicine (33 R = H) and not the other possible cyclization product (53). 

R. Adams (20). In the first case (15) o-nitrobenzyl chloride reacted with methyl y-aminobutyrate to give iV-o-nitrobenzylpyrrolidone, which by reduction to the amine and cyclization with phosphoryl chloride afforded the desdred product (VII). Its identity with desoxyvasicine was further confirmed by reduction to dihydrodesoxyvasidne (pegan, IV). 

The corresponding o-nitrobenzyl chloride 43b catalyzed the asymmetric addition of thiophenol to 2-cyclohexen-l-one under solid-liquid PTC conditions (e.e. up to... 

Recently Vanelle reported the first example of a SnAt reaction using TDAE-initiated carbanions in fluorinated quinazoline series. The o-nitrobenzyl carbanion 1200, formed by the action of TDAE on o-nitrobenzyl chloride 1197, reacts with 4-chloro-2-trifluoromethylquinazoline 1198 via a SnAt mechanism affording 4-benzyl-2-trifluoromethylquinazolines 1199. The reaction as electron withdrawing group-dependent and in a case of non-fluorinated analogue of 1198 does no work (Scheme 257) [741]. 

---