Suvniwwy Household bleach (sodium hypochlorite) generates ruthenium tetroxide from its lower valence states.

A reexamination of the literature on inter and intramolecular reactions of amines with N-substituted phthalimides has led to the demonstration that methylamine is a convenient reagent for removal of a phthaloyl protecting group from nitrogen at room temperature. Application of this procedure (first described in 1896) to the Gabriel synthesis of primary amines and to peptide synthesis is recommended. The simplicity of the reaction is a consequence of the consecutive occurrence of two unexpectedly rapid processes: (1) methylaminolysis of one of the imide bonds; (2) intramolecular catalysis, by an N-methylamido group, of the hydrolysis or aminolysis of an adjacent phthalamido linkage.Some unsuccessful attempts to prepare 2-aminoethylphthalimide are also described.

. Can. J. Chem. 56, 1423Chem. 56, (1978. It has been shown that phosphorus pentasulfide (P,Slo) is a mild, effective reagent for the reduction of sulfoxides to sulfides and that this conversion can be achieved selectively in the presence of other reactive groups such as ketone, ester, amide, nitro, and halogen. Phosphorus pentasulfide also appears to be a promising reagent for reducing selenoxides but is ineffective in reducing sulfones, sulfinates, o r sulfites. 1 There has been a great deal of current interest in i devising new reagents for both the mild, selective I oxidation of sulfides to sulfoxides (1, 2) and, to an i even greater extent, for the reverse process of reduc-

The sulfoxides derived from 2,3-dihydro-4H-naphtho[1,2-b]thiopyran and its 4-phenyl and 4-oxo derivatives, as well as the analogous sulfoxides in the 2,3-dihydro-1H-naphtho[2,1-b]thiopyran series, have been synthesized and their structures established by spectroscopic methods, especially 1H and 13C nmr. On photolysis these sulfoxides have been found to react by a rather inefficient photochemical deoxygenation pathway.

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