ether methyl and/or ring substitution under the reaction conditions. When the product mixture from a toluene-anisole chlorination is treated with ethanolic KOH at rooin temperature, one of the product peaks is completely converted to a new gas chromatographic peak of longer retention time, while a peak with the same retention time as benzyl chloride is converted to a material of the same retention time as benzyl ethyl ether at a much slower rate. Treatment of the product mixture with aqueous silver nitrate results in rapid loss of the same peak as above and the formation of material of the same retention time as phenol and the formation of material of the same retention time as formaldehyde. These qualitative results are consistent with the presence of chloromethyl phenyl ether in the product mixture (cf. ref. 5). In addition, a trace of material with the same retention time as a mixture of chloroanisoles was noted. These results strongly suggest that related reactions also occur with p-methylanisole. That this is so was demonstrated by mixing a product mixture with alcoholic KOH. Within 10 min after mixing, one product gas chromatographic peak had been destroyed and a new peak had appeared. A second peak was also destroyed with concomitant formatioil of another at a rate slower than the first. It is clear that p-methoxytoluene is destroyed by processes competitive with benzylic hydrogen abstraction.Using the value obtained in this work for p-phenoxytoluene and the previously unknowil value for p-fluorotoluene (Table I), along with the values reported previously by one of us (3), the following correlations2 were obtained: log k / k , = -0 . 7 6~ -.00; s, 0.045; r, 0.983; log k/ko = -0.60o' -.06; S, 0.073; r, 0.954.Including the values for nz-and p-nitrotoluene (1) Sodium borohydride reacts with sulfur at room temperature in the presence of appropriate organic solvents to give a sulfurated borohydride: NaBH2S3. The formulation of this hydride has been established by infrared, nuclear magnetic resonance, and elementary analysis. Thermal deco~nposition and hydrolysis are reported. The reaction observed with NaBH, appears to be general between borohydridcs and the lower elements of Group VIA: Se and Te. A facile preparative method of NaBH,S, is presented.