Nitrogen oxychloride

Nitrosyl Chloride(Nitrogen Oxychloride), NOC1 mw 65.47, orn-red gas with a chlorine-like... 

NITROGEN OXYCHLORIDE (2696-92-6) Incompatible with water, producing hydrochloric acid solution and toxic red oxides of nitrogen. Acids or acid fumes produce highly toxic chloride fumes. Aqueous solution is incompatible with sulfuric acid, alkalis, ammonia, aliphatic amines, alkanolamines, alkylene oxides, amides, epichlorohydrin, isocyanates, ni-tromethane, organic anhydrides, vinyl acetate. Corrodes aluminum, austenitic stainless steels (causing pitting attack and stress corrosion), and other metals in the presence of moisture. 

Nitrogen oxide chloride Nitrogen oxychloride. See Nitrosyl chloride... 

Eschenmoser and co-workers <20030L2067, 20040L3691, 2005HCA1960> carried out thorough synthetic studies for preparation of some imidazo[l,5-tf][l,3,5]triazines with particular substitution patterns such that these compounds could be considered as nitrogen-positional isomers of some nucleobases. One of the typical synthetic steps is treatment of the diaminotriazine derivative 248 with phosphorus oxychloride to give the cyclized purinoid 249 in high yield (82%). Modification of this procedure also allowed preparation of the various oxo- and amino-related derivatives 250-252. 

Treatment of the hydrazide 59 with ethyl orthoformate causes an intramolecular N-acylation resulting in the tetracycle 60. The conversion of 1,4-diphenylcarbazole into 61 using N-methylformanilide-phosphorus oxychloride at 95°C must involve an oxidation at some stage. Heating car-bazole with diphenyl 2-benzylmalonate, diethyl 2-ethylmalonate, or malonic acid-phosphorus oxychloride produced the tetracycles 62 (R = PhCH2, Et, and H, respectively). It is not clear whether the N-9 or the C-1 acylations required for the formation of 62 occur first, although it is likely that the initial attack is at the nitrogen. 

The degradation of a-aminocarboxylic acids has proven to be a useful method for the preparation of iminium salts. For example, treatment of N- methylpipecolic acid (97) with phosphorus oxychloride gave 94% of the iminium salt (98) (Scheme 7) (76JA7448). The synthetic utility of this approach is illustrated by the synthesis of tetrahydroberberine (Scheme 8) (78JOC2115). The advantage of this method for the preparation of iminium salts is that the position of the carbon-nitrogen double bond can be controlled. 

Treatment of piperazine-2,5-diones, unsubstituted on the nitrogen atoms, with phosphorous oxychloride results in chlorination with simultaneous aromatization by loss of two hydrogen atoms [82JCS(P1)953] as shown in Scheme 16. 

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