The 15N-lH coupling constants in some amino-present some new W -H spin coupling data which are phosphines, aminoarsines, and sulphenamides have been relevant to these questions. determined.The appropriate =N-labelled compounds (Table ) were prepared by substituting 96-57' enriched 15NH3 for 14NH3 phine, (CH,),NPF,, has revealed a trigonal planar geometry about nitrogen and an unexpectedly short P-N bond distance. These findings have raised two important but related questions: (a) is trigonal planar nitrogen a general These results suggest that the nitrogen atoms are approxistructure feature of aminophosphines, aminoarsines, and mately trigonal planar in (CF,) ,PNH,, [CF,S] ,NH, and the sulphenamides? and (b) what is the importance of multiple phosphorane PF,(NH,),. On the other hand, the aminobonding in the N-X bonds of these compounds ? We arsines, the methyl-substituted aminophosphines, and 7 0 2s = I 0.43 J("N-H) -6

Evidence is presented for the generation of cyclobutadiene dianion, a Huckel aromatic, from cisdichlorocyclobutene and sodium naphthalide ; although highly reactive, the dianion can be deuteriated to afford 3,4-dideuteriocyclobutene.

Use of Halogen-Sulfide Complexes in the Synthesis of Indoles, Oxindoles, and Alkylated Aromatic Amines Sir:Recently, we reported on the reactions of iV-chloroanilines (1) with dialkyl sulfides, ß-keto sulfides, and -carboalkoxy sulfides to yield intermediate azasulfonium salts, which on treatment with base produced methylthiomethylanilines (2),1 3-methylthioindoles (3),2 and 3-methylthiooxindoles (4)3 in good to excellent yields. Raney-nickel desulfurization of these products gave o-alkylanilines, indoles, and oxindoles, respectively. A major limitation of this surprisingly general synthetic process was associated with the instability of the A-chloroaniline when X was a cation stabilizing group such as p-methoxy. As we have previously shown, A-chloro-p-anisidines are extremely reactive,4 even at temperatures as low as -78°. Thus, our original procedures1-3 were not readily applicable to the synthesis of 4-methoxyanilines, 5-methoxyindoles, or 5-methoxyoxindoles. In view of the importance of methoxylated natural products related to the desulfurized versions of 2, 3, and 4, we now wish to report a major modification of our original synthetic concept which permits the preparation of the desired methoxylated compounds.Mechanistically, the reaction of W-chloroanilines (1) P.

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