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NICK HENRY WERSTIUK, DOUGLAS NEVE BUTLER, and SUSHIL DATTA. Can. J. Chem. 64, 760 (1986). The ultraviolet photoelectron spectra of 2,7-diazatetracyclo[3.3.3.0~~90.g~"]undecane (1) and its N,N-dimethyl-and methylene-bridged analogues 2 and 3 are documented. The spectrum of 2, which exhibits a nitrogen lone-pair splitting of 0.95 k 0.1 eV, is interpreted on the basis of an interaction of "inside" lone pairs of the 1,2-diamine. Apparently this is the first report of a study of such an interaction. The spectrum of 1 is consistent with our view that 1 is an intramolecularly hydrogen bonded species in which the lone pairs are "inside-outside".NICK HENRY WERSTIUK, DOUGLAS NEVE BUTLER et SUSHIL DATTA. Can. J. Chem. 64,760 (1986). . .On a mesurC les spectres photdlectroniques ultraviolets du diaza-2,7 tCtra~~cl0[3.3.0?~~0.~~"]undCcane (1) et de ses analogues N,N-dimCthylC (2) ou portant un pont mCthylCnique (3). Le spectre du compost 2 prtsente un couplage de la paire d'Clectrons libres de I'azote de 0,95 k 0,l eV que l'on interprkte sur la base d'une interaction des paires d'Clectrons "internes" de la diamine-l,2. Le spectre du composC 1 est en accord avec notre hypothese selon laquelle ce composC est une espkce qui posskde des liaisons hydrogenes intrarnolCculaires dans lesquelles les paires libres sont du type "inttrieur-extCrieurV.[Traduit par la revue] Introduction Over the past fifteen years, studies of nitrogen, oxygen, and sulfur compounds by ultraviolet photoelectron spectroscopy have yielded a wealth of information on the factors that determine the magnitudes of through-space and through-bond interactions of lone pairs. Studies of diamines have been especially fruitful (1). In a significant paper in 1970, Heilbronner and Muszkat (2) confirmed early EH and MIND012 calculations that predicted significant interaction between the

Oxalodinitril-bis-arylimine 2 konnen aus den entsprechenden Hydrazidchloriden durch Dehydrohalogenierung in situ dargestellt und mit Dipolarophilen abgefangen werden. In Abwesenheit der letzteren dimerisieren 2 (Aryl = Phenyl oder o-Tolyl) zu meso-ionischen 1.2.4.5-Tetraaza-pentalenen 17, einem bisher unbekannten heteroaromatischen System. Das sterisch stark gehinderte 2c (Aryl = 2.6-Dimethyl-phenyl) lagert sich intramolekular in 2-[2.6-Dimethyl-phenylimino]-2-[7-methyl-indazolyl-(2)]-acetonitril (25) um. Der Mechanismus dieser Reaktionen wird diskutiert. Rearrangement of Oxalodinitrile-bis-aryliminesThe title compounds 2 are obtained in situ from the corresponding hydrazidehalides by dehydrohalogenation and may be trapped by suitable dipolarophiles. In the absence of the latter, they dimerize (if aryl = phenyl or o-tolyl) to mesoionic 1,2,4,5-tetraazapentalenes 17, a so far unknown heteroaromatic system. The strongly sterically hindered 2c (aryl = 2,6dimethylphenyl) undergoes intramolecular rearrangement to [7-methylindazolyl-2]-[2,6dimethylphenylimino]-acetonitrile (25). The mechanisms of these reactions are discussed.

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The structures of a number of polycyclic diamides available via the action of ammonia on exo,exo-5,6-dibromonorbomane-endo,endo-2,3-dicarboxylic anhydride have been shown to be incorrectly reported. These substances all possess a nortricyclyl skeleton, e.g. 8, 9, and 10.