Pseudohalides bonding

R = organic group, X = bromide or iodide, X = pseudohalogen, i.e., cyanide, isocyanate, fulminate, isothiocyanate, isoselenocyanate, dicyanamide and azide. Other organogermanes containing germanium-pseudohalide bonds are listed in Chapters 3 8.2 and k.l.k. 

Nucleophiles like alcohols [2, S], hydrogen sulfide [2], thiols [2,10], ammonia, amines, hydrazines, hydroxylamines [2 11, 12, 13, 14, 75], azides [2], other pseudohalides [2], phosphonates [2,16,17,18,19, 20], and phosphanes [2,19] add rapidly across the CO or CN double bond to yield stable adducts The phosphonate adduets undergo a subsequent aleohol—lester rearrangement [19, 20] (equation 2)... 

Iqbal Z (1972) Intra- and Inter-Molecular Bonding and Structure of Inorganic Pseudohalides with Triatomic Groupings. 10 25-55... 

The synthesis of metalloporphyrins which contain a metal-carbon a-bond can be accomplished by a number of different methods(l,2). One common synthetic method involves reaction of a Grignardreagent or alkyl(aryl) lithium with (P)MX or (PMX)2 where P is the dianion of a porphyrin macrocycle and X is a halide or pseudohalide. Another common synthetic technique involves reaction of a chemically or electrochemically generated low valent metalloporphyrin with an alkyl or aryl halide. This latter technique is similar to methods described in this paper for electrosynthesis of cobalt and rhodium a-bonded complexes. However, the prevailing mechanisms and the chemical reactions... 

The validity of reaction Scheme 1 is not limited to heterolyses of covalent bonds to carbon. It covers also cases where both X and Y are hetero-atoms (e.g. oxidation of halides and pseudohalides by OH, cf. Ref [40] or where X is a hetero atom and Y is a metal (cf. Ref [41])... 

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