Correlation of molar refraction with the first order molecular connectivity index was found to be excellent for alkylsilanes of molecular formula SiC,H2,+, , which include tetraalkylsilanes, trialkylsilanes, dialkylsilanes, and monoalkylsilanes. The separate correlation of molar refraction with the first order molecular connectivity index for each of these four classes of alkylsilanes was also found to be excellent. Excellent correlations were also obtained using an empirically determined first order valence molecular connectivity index. It is shown that the first order molecular connectivity index gives more satisfactory predictions of molar refraction than does the empirically determined first order valence molecular connectivity index.
Excellent structure‐molar refraction relationships of alkylphosphines, dialkyl sulfides, alkylthiols, alkylamines, dialkyl ethers, and aliphatic alcohols were obtained using the Randic molecular connectivity index. Excellent structure‐molar refraction relations were also obtained using two empirically‐modified connectivity indices which reflect either the difference in bond length between the heteroatom‐carbon bond and a carbon‐carbon bond or the difference in covalent radius between the heteroatom and a carbon atom. Use of the empirically‐modified indices improves the prediction of molar refraction for a mixed set of alkylphosphines, dialkyl sulfides, alkylthiols, alkylamines, dialkyl ethers, aliphatic alcohols, alkanes, alkylsilanes, alkylgermanes, and alkyl halides.
The ability of triphenyltin hydride to convert organic halides and amines to the corresponding hydrocarbon and triphenyltin halide and hexaphenylditin, respectively, is a relatively new development in organotin chemistry. l~~ In connection with a study of the stereochemistry of these reactions currently being carried out in these laboratories, it was necessary to see if triphenyltin hydride would satisfactorily react with dl-a-phenethyl chloride and dl-a-methylbenzylamine. It was also considered of interest to study the reaction of triphenyltin hydride with benzyl chloride and benzylamine.The experimental procedure employed was similar to that reported for the reaction of triphenyltin hydride with allyl bromide and allylamine.3 The reaction of triphenyltin hydride with benzyl chloride gave triphenyltin chloride (65.6%) and toluene (25.5%). With dl-a-phenethyl chloride there was obtained triphenyltin chloride (68.4%) and ethylbenzene (79.4%).The reaction of triphenyltin hydride with benzylamine in the molar ratio of 2 : 1 gave hexaphenylditin (75.8%), toluene, and ammonia. With dl-amethylbenzylamine there was obtained hexaphenylditin (52.7%) and ammonia.The liquid products were isolated by distillation of the reaction mixture and were identified by the fact that their infrared spectra were superimposable upon those of authentic samples. No attempt was made to separate quantitatively the liquid product from the solid. In the case of benzylamine the mixture was distilled only until enough of the liquid was obtained for an infrared spectral determination. In the case of dl-a-methylbenzylamine, ethylbenzene was probably formed, but it was not isolated. In this reaction an amount of unchanged dl-a-methylbenzylamine was isolated which was consistent with the yield of hexaphenylditin. The solids were isolated as quantitatively as possible and were identified by the fact that admixture with authentic samples did not depress the melting points.In each of the above reactions a small quantity of tetraphenyltin was isolated. This compound may have been formed from unchanged triphenyltin hydride during processing of the reaction mixture. It is reported that triphenyltin hydride is decomposed by air and by exposure to light with separation of tetraphenyltin.* EXPERIMENTAL Melting points were determined in open capillaries and are uncorrected. All the reactions were carried out in a nitrogen atmosphere.6 Reaction of triphenyltin hydride with benzyl chloride.Triphenyltin hydride' (30.0 g., 0.0854 mole) was added to a dry 5 0 4 . flask fitted with a Claisen head, thermometer, and condenser. F'reshly distilled benzyl chloride (10.8 g., 0.0854 mole), b.p. 176", was added in one portion, and the system was evacuated. The reaction mixture was placed under 1 atm. of nitrogen and then was heated with occasional shaking a t 80' f 5' for 4 hr. After 4 hr. a colorless crystalline material was evident in the reaction mixture.The mixture was distilled a t atmospheric pressure (pot temperature to 140'). The distillation was stopped when the r...
Die Isocyanate (I) reagieren mit den Stannylcyanamiden (II) bzw. (IV) zu den N′‐Cyan‐O‐(triorganostannyl)‐isoharnstoffen (III) bzw. (V), von denen die Triphenylstannglverbindungen (V) gegen Pilze wirksamer sind als die Trimethylstannylverbindungen (III).
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