ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
The Reaction of Aromatic Diazocyanides with Diazoalkanes; a Class of Stable Crystalline Azomethine IminesAs first reported in 1960, electrophilic attack of aromatic anti-diazocyanides on diazofluorene, diphenyl- or 4,4′-dimethoxydiphenyldiazomethane produces crystalline C,C,N α-triaryl-N β-cyano-azomethine imines in high yield with elimination of nitrogen. The compounds 13-20 are the first stable representatives in which the azomethine imine system is not incorporated in an aromatic ring. The vibrational and electronic spectra exclude the alternative diaziridine structure. C-(2,2′-Biphenylylene)-Nα-(4-bromophenyl)-Nβ-cyano-azomethine imine shows a dipole moment of 6.7 D. The bond lengths of azomethine imines are discussed.
Notes:
Wie 1960 erstmals berichtet gelangt man durch elektrophilen Angriff aromatischer anti-Diazocyanide auf Diazofluoren, Diphenyldiazomethan und dessen 4,4′-Dimethoxy-Derivat unter Stickstoffabgabe zu den kristallinen C,C,N α-Triaryl-N β-cyan-azomethiniminen 13-20; dies sind die ersten stabilen Vertreter, in denen das Azomethin-imin-System nicht Teilstück eines aromatischen Rings ist. Die Schwingungs- und Elektronenspektren schließen alternative Diaziridin-Strukturen aus. C-(2,2′-Biphenylylen)-N α-(4-bromphenyl)-N β-cyan-azomethinimin zeigt ein Dipolmoment von 6.7 D. Die Bindungslängen der Azomethin-imine werden erörtert.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19771100213
