The use of iodine in triethylamine is presented as a superior alternative to the commonly used silver oxide procedure for the oxidation of diaziridines to diazirines. However, in acidic media this oxidation is not stoichiometric. A study of the iodine-iodide ion redox system with 1,1-hydrazicyclohexane disclosed that a catalytic cyclic process is operative and leads to disproportionation of the diaziridine. Conversely, overconsumption of iodine under conditions of rapid titration is also possible, perhaps owing to the formation of an N,N '-diiododiaziridine intermediate. A variety of simple diazirine-containing aliphatic acids, acid chlorides, esters, alcohols, acetals, aldehydes, amines, amides, etc., were prepared either from the corresponding ketone or by subsequent transformations. The diazirine group was stable to a variety of reagents. The physical properties (pK", uv, ir, nmr) of some of these functionalized diazirine-containing molecules are discussed. The effect of the diazirine function on p.Ka is approximately comparable with that exerted by a keto group or a chlorine atom, but it is less diminished by increasing distance.

remove thiophenol and then extracted with Claisen'a alkali (three 100-ml portions). The latter extracts were diluted with water, neutralized with carbon dioxide, and then extracted with hexane. The combined hexane extracts were dried and concentrated to give 2.68 g (91%) of a 43:57 mixture of 8(11)and 8-.An analytically pure sample was obtained by elution from silver nitrate-silica gel: nmr (CDC13) 9.12 (t,

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