Zur Kenntnis der Diazohydrazide

Abstract

ab und fallt :IUS dem Filtrnt die I -P h e n y l -t e t r a z o l -4 -c a r b o n -Y ii 11 r e , CsHs. i. N: N. C(CO9H) :k, mit Salzslure aus. Die Ausbeute betrHgt 70 O/O der Theorie. Die Saure erwies sich in allen Eigensrliaften ideutisch mit der von B l a d i n I), W e d e k i n d l ) , sowie D i n i r o t h unil D i e n s t b n c h 3, beschriebenen Substanz.Versuche, das intermediiir entetehende T r i b r o m b e n z o l -a z oo x nl s a 11 r e -ph e n y 1 h y d r a z i d i n zu fassen, schlugen fehl. Unterbricht man die Reaktion vor der Vollendung, so erhHlt man eine Fiillung, die aue einem Gemenge von unveriindertem Tribromphenylazitl, yon Tribromanilin und aus roten Krystnllen besteht, welch IetLtere zweifellos das g e~u c h t e Zwischenprodukt sind. Sie sind aber so \erlinderlich und zerlallen 80 leicht in Tribromanilin und das Natriumsalz der Phenpltetrazolcarbons8ure, dafl man sie nicht i n reiner Form iaolieren kann.--- Otto D i m r o t h und G u i l l a u m e d e Yontmollin:Zur Kenntnie der Diasohydradde. (Eingcg. am 17. Oktober 1910; mitget. in dor Sitzung von Hrn. E. Benary.) Die in der vorhergehenden Abhandlung beschriebene Spnthese yon Derivaten des 1 . 2 . 3 . 5 -T e t r a z o l s ist ein Analogon der 1.. P e c hmnnnschen Synthese \*on O s o t r i a z o l e n aue Oeazonen. I n beiden PBllen schliebt sich der Funfring zusammen, indem aus der offenen Kette Anilin abgespalten wird: Es schien verlockend, aut diesem Pfad noch den letzten Schritt writer zu gehen und zu versuchen, die Kette von G Stickstoffatomen zii sj-nthetisieren und dunn durch Abspnltung yon Anilin zu Abkommlingen des P e n t a z o l s ' ) zu gelangen: I) Diese Berichte 18, 2908 [1885]. 3 Diese Reiichtc 81, 947 [1898]. . 3) Diesc Berichte 41, 4066 [190S]. ') Fritlierc Ycisixhc ziir Daistellunfi yon Pentazol: H n u t z s c l i , diese L4clite 36, 30.X [1903].

Stabilization of the Dual-Aromatic cyclo-N5– Anion by Acidic Entrapment

“…11,[23][24][25][26][27][28] The development of a synthetic route to cyclo-N5ˉ has a history full of hardships. It started in 1903 29 and experienced failure 30 , misunderstanding 31 , and dispute 32 in the following decades. In 2002, cyclo-N5ˉ was first detected with electrospray ionization mass spectrometry but existed only fleetingly in gas 33 .…”

“…11,23−28 The development of a synthetic route to cyclo-N 5 − has a history full of hardships. It started in 1903 29 and experienced failure, 30 misunderstanding, 31 and dispute 32 in the following decades. In 2002, cyclo-N 5…”

“…However, the long pursuit of an energy-intensive material, the inorganic pentazole anion cyclo -N 5 – , although known to be π-aromatic, is surprisingly unstable, difficult to obtain, and susceptible to electrophilic attack. ,− The development of a synthetic route to cyclo -N 5 – has a history full of hardships. It started in 1903 and experienced failure, misunderstanding, and dispute in the following decades. In 2002, cyclo -N 5 – was first detected with electrospray ionization mass spectrometry but existed only fleetingly in the gas phase .…”

Bitter sweeteners: tetrazole derivatives of arylsulfonylalcanoids – synthesis, structure and comparative study

“…Tetrazoles can be obtained from the corresponding carboxylic acids by reaction of amidrazones with nitrous acid (Pinner, 1897), by reaction of diazonium salts with acylhydrazides or S-diacylhydrazines (Dimroth & de Montmollin, 1910), and by condensation of phenyl azides with the phenylhydrazones of aldehydes in alcoholic sodium alkoxide solutions (Dimroth & Merzbacher, 1910). The synthesis of some arylsulfonylmethyltetrazoles was described previously by MacManus (1969).…”

Kinetic Stability of Pentazole

“…The synthesis of pentazoles has faced many challenges over the last century. After repeated failures, , the first reported synthesis in 1915 was quickly discredited, and it was only in 1956 when Huisgen and Ugi reported their arylpentazole synthesis . Nearly half a century later, the parent pentazole (R = H) was synthesized in 2003 by Butler, Stephens, and Burke .…”