Phenyltin bromides

Boron tribromide is not appropriate in these experiments as it will not be easily freed from phenyltin bromide which has the same volatility. 

Phenylethynyl)trimethylstannane, Sn-00218 Phenylfluorogermylene, see Ge-00067 Phenylgermane, Ge-00068 Phenylgermanium trichloride, see Ge-00066 Phenyllead trifluoride, see Pb-00045 (Phenyl phenylphosphonato)trimethyltin, Sn-00295 a-(Phenylphosphonato)trimethyltin, Sn-00184 Phenylstannane, Sn-00107 1-Phenylstannatrane, see Sn-00242 Phenylstannonic acid, Sn-00104 (Phenylstannylidyne)tris(diphenylarsine), see Sn-00459 Phenyltin bromide dihydride, see Sn-00105 Phenyltin sesquisulfide, see Sn-00382 Phenyltin trichloride, see Sn-00100... 

A procedure was developed by Gauer et al for the determination of various cyclohexyltin bromides. It was not, however, applicable to the phenyltin bromides due to their low volatility. 

Phenyl isocyanate, conversion to di-phenylcarbodiimide, 43,31 Phenyl isocyanide, 41,103 Phenyllithium, reaction with allyltri-phenyltin, 41, 30 standardization of, 41, 32 Phenylmagnesium bromide, 41, 91 reaction with ( r(-butyl perbenzoate, 41,91... 

In 1973, Taddei succeeded in preparing optically active (+)-benzyl-z-propylmethyl-phenyltin, (+)-(62), by a reaction of the optically unstable z -propylmethylphenyltin menthoxide with benzylmagnesium bromide U) (see Table 4). This asymmetric induction very probably does not yield an optically pure compound but is a very rapid and facile route to optically active organotin compounds of unknown optical purity. 

Electrophilic addition to 9-vinylcarbazole occurs in the Markovnikov sense, thus hydrogen chloride,hydrogen bromide,chlorine, and bromine in carbon tetrachloride, and iodine chloride in pyridine are recorded as adding with initial electrophilic attack at the methylene. Mercuric acetate in methanol gave 9-(2-acetoxymercuri-l-methoxyethyl)carbazole. Although 9-vinylcarbazole gave an iodohydrin, comparable reaction with methanolic sodium hypochlorite led to 9-(2-chlorovinyl)carbazole. Catalytic reduction of the latter produced 9-(2-chloroethyl)carbazole. Tri-phenyltin hydride gave 96. ... 

Some other triorganotin monochlorides are not associated in the solid state. Tri-phenyltin monochloride (Sn-Cl 2.353 A) [186] was described as discrete unassociated in the solid state and even tricyclohexyltin chloride was first described as monomeric [187], like the triorganotin bromides and iodide investigated so far (see Table 4.1). Tris(m-tolyl)tin chloride (Sn-Cl 2.379 A) and tris(3,5-dimethylphenyl)tin chloride (Sn-Cl 2.357 A) are also discrete monomers [187a]. 

Certain limitations have been noted. Allyl bromide (48), crotyl chloride (56), and a-methylallyl chloride (56) undergo reduction to the corresponding alkenes, rather than addition to the double bond, upon reaction with tri-phenyltin hydride. Similarly, propargyl bromide (55) is reduced by tri-n-butyltin hydride. The presence of amino groups in the olefin may in some... 

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