Materials Restwch, Central Research I)ivision, The National Cash Register Company ' l~t i r w dif'f'erent 3,iE-diacylfuroxans (1) are shown to give :i-substituted-J -phenyl-4,5-dioximino-2-pyrazolines (2) upon reaction with phenylhydrazine. The compounds 2 were dehydrated t o O-sut~stitutt:d-4-phenyl-~~~f-pyrazolo~:~,4~] furazaris. (3) and thermally converted t o :{-substituted .. 5-iminoanilino-iE-acylfurazans (10).l'c.rkin ( 1) trt:att:d methyl dimethy1acc:toacetate with nitric: acid to obtain a "glyoximc: peroxide" that with phenylhydrazine gave "methyl phenylaminoisotriazoxole-tJimethylmalonylate"; this in turn upon treatment with aqueous hase gave an acid of semi-empirical constitution ( l 6 t I 5 [ ( : 3 N 4 0 ] ( :~l e 2 ( ; 0 2 t 1 to which it was "difficult to assign a satisfactory formula". Perkin suggested a structure containing a I ,5 -dehydro (valence -bridged)-I Jdihydro-I ,?J,iE-tetrazine nucleus, whose improbability has previously been noted (2). Our curiosity as to the structure of the acid led us to rcirivtstigate these arid related reactions. h ' e assumed that tht: "glyoxime peroxide" was in fact Ic, a ;i,il.-diacylf'uroxan ( 3 ) , and thus for comparison purposes we began liy rt:-examining the reported reactions of' the diacetyl and dilttxizoyl furoxans. 1)iacetylfuroxan (Ib) has been reported (4) to give with 1iniitt:d or excess phenylhydrazine merely the monophenylhydrazone (m.p. I f) I -162") o r the diphenylhydrazone (1n.p. 176"), rt:spectively. liowevt:r, neither elemental analyses nor any chemical evidence for these assignments were given. 1)itwizoylfuroxan ( l a ) reportedly reacts with phenylhydrazine to give benzoylphenylhydrazine and a yellow material (2a) of empirical formula 5 I1 N 4 0 2 , which upon heating in acetic acid or acetic anhydride affords a diff'erent substance (3a) heretofore formulated as an isomer of 2a (5) o n the basis of a single nitrogen analysis.Formulas A , H, and (; have been proposed as structures for 2a and 3a, and thert: has been extensive discussion as t o which formula should be assigned to which compound (5-8).1 he initial unstahle reaction product of l a and phenyl-r .The compounds 1 react with aniline to give :Ihydrazine was presumed to have structure 4 (5Jj). This formula, which implies addition of one molecule of phenylhydrazine t o a carbonyl group and one to the ring (;=N+O function, could readily give A and H, and lead t o C after a single Heckmann rearrangement.

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Während die Reaktion zwischen a,a‐Diphenylchloracetylchlorid (I) und dem Dimethylhydrazin (IIa) lediglich das Cyclisierungsprodukt (IIIa) liefert, er: hält man mit Hydroxylamin‐O‐methyläther (IIb) neben (IIIb) über (IV) und (V) das Umlagerungsprodukt (VIb).