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Triazines

TRIAZINES, in organic chemistry, a series of cyclic compounds, containing a ring system composed of three carbon and three nitrogen atoms. Three series are possible, the positions of MARINE TRIAS or THE ALPINE AND INDIAN TYPES.

German Trias.

England.

North Alpine Region.

South Alpine Region.

Alpine Zone Fossils.

India.

America.

Sandstones Rhaetic or Penarth Kossen Rhaetic Kossen Magalodon limestone .0 and Clays S with Avicula contorta beds White Lias, black pa- E"O .a beds Dachstein beds o Lithoden- Kalk and (Azzarola J3 dronKalk Dolomite beds)

Avicula contorta and " Hochgebergskalk " in part Star Peak beds per-shales, Bone bed marls Bone bed ttjl Aulacothyris limestone Sandstones with dino- ,, Stubensando. stein Red and mottled * J/ ' _, Dachstein 2 Dachstein Sagenites beds sa u r s of Connecticut marls with Kalk and -| -2 Kalk and Turbo Coral lime- rock - salt V.'SlD Coral -a o Coral (Worthenia)

stone and gyp- 2 S*""' 2 Z limestones c .c limestones solitarius ,? Schilfsand- Sen .2 Halorites stein Variously i i beds O 0, % Grenz dolomite jj Lettenkohlen - coloured sandstones and marls (with"Wa- C J OH a Opponitz 5* e limestone and .2 dolomite Raibl beds Tropites subbullatus Hauerites beds o< c -5 Taylorville beds of California e sandstein j: D olomi t ic ter-stones") Conglomer- '^ % a Reingrabner y beds and TJ Trachyceras aonides Spiti dolomite j limestones ^ and marls ate and breccia Lunz sand- .0 stone cs liiil Daonella beds Sandstones with plants, Haupt- Muschelkalk c-o c ^ c .2 O C u - o ^ e Reifling M ! - J .2 limestone c c ~o a rtT3. Cassian e^-3 g'se beds j> o S oj.5 Wengen Trachyceras aon Daonella Daonella beds Richmond, Virginia jD.SJH ;| and Part- '5- g-2 A g g beds lommeli "O CJ nach beds g -o t/5u]Slxi Buchen- Protrachyce- Anhydrite group, (^ M "^ S g stein ras reitzi dolomite and : j='C (O *^ .2 j> *-> g beds J= marls with rocksalt and gypsu m c c *^* rt 13^.

2 Trinodosus beds E (Prezzo lime- Ceratites trinodosus Ptychites beds 2 'C Koipato beds c .| "Alpine o ^ u stone)

3 *;-" Zellendolomit V w VJ Muschel- -2 "g.- (Brachiopod 3 <5 s J ka'k" | limestone) i.3 Wellenkalk and ; (part)

'5 g" 13 7.3 Recoaro * u "'3 limestone " Ihynchenella decussata Niti lime- dolomite Z o o "" Gutten- 1C Sjs Virgloria *o c stone c 1 " S stein beds 06 | limestone ^g S o J /\ ^ __ _^_ - _ UJ r^i Hedenstro- cu Meekoceras Upper division Upper mot- (d<3 Campil beds Campil beds Natiria emia beds c" rt.

beds, Idaho or Roth tled sand- costata Prinolobus ^ stone Middle division Pebble beds .5(7! 2 C "S Seis beds Seis beds Pseudomono- beds t/)

or Hauptsand- t^ &" Pj-f tis clarai OtOCCTdS ffl stein and ( Vosgesensandstein) Lower division Lower mot- v- en M OJ beds "O (Permian) ^ c a sandstones with tled sand- occasional oolite stone (Rogenstein)

the various units of the ring system being illustrated in the annexed formulae :

c c c C/\C C \/ N N 5f a-Triazines, /3-Triazines, Cyanidines.

Few simple derivatives of the o-series are known, those which have been prepared result by such reactions as the condensation of aminoguanidine or a similar type of compound (e.g. semicarbazide) with ortho-diketones (J. Thiele, Ann., 1898, 302, p.

299):

/NH-NH 2 OC-CaHs /NH-N^ HN:C< + I -> HN:C< >C-C 6 H 6 ; \NH 2 OC-C 6 H 6 \N = C^CeHs Wolff has obtained a chloro-derivative by the action of potassium cyanide on diazoacetophenone and subsequent treatment with acid. The phen-a-triazines are more numerous, and are obtained either by the action of concentrated acids on the formazyl compounds (E. Bamberger, Ber., 1893, 26, p. 2786): C 6 H 6 N:N- X /N:N C 6 H 6 -NH-N^ C \N:C-COC6H 6 ; by the reduction of symmetrical acyl-ortho-nitrophenyl hydra - zines (e.g.;NOrC 6 H 4 -NH-NH-CHO); or in the form of dihydro derivatives by the condensation of aldehydes with ortho- aminoazo compounds (H. Goldschmidt and Y. Resell, Ber., 1890, 23, p. 487), or from the aminoazo compound and a mustard oil, the resulting thiocarbanilido derivative being heated with acetic acid (M. Busch, Ber., 1899, 32, p. 2960):

.N-C(SH):N-C 6 H 6 x.N-C:NC,H 6 C,H,f -> C7H 6 f +H 2 S.

C. Harries (Ber., 1895, 28, p. 1223) has also shown that as-phenylhydrazino-acetic esters, when heated with formamide and substituted formamides under pressure, yield dihydrotriazines:

C0 8 R 4_R'NH THO ^ CO NR' CH CH 2 -N(C 6 H 6 )NH 2 + * CH,-N(C,H 4 )-N The phen-a-triazines are yellow-coloured crystalline compounds of a somewhat basic character.

Derivatives of /3-triazines are formed by the action of nitrous acid on ortho-aminobenzylamines (M. Busch, Ber., 1892, 25, p. 445), or in small quantity by the action of nitrous acid on ortho-aminobenzoylphenylhydrazines (A. Konig and A. Reissert, Ber., 1899, 32, p. 782), the chief product in this latter reaction being an isoindazolone:

/CH 2 -NHC 6 H S /CHrNH-CeHs /CH 2 -NC,H 6 C 6 H/ -=>C 6 H 4 < ->C 6 H/ | N N=N aeHi-c NH 8 -HC1 The best drawn series of the triazines is the symmetrical or cyanidine series, members of which result from the condensation of acid anhydrides with aromatic amidines (A. Pinner, Ber., 1892, 25, p. 1624) :

*KH ^N-C^-CeHa -f +(CH 3 co) 2 o^c 6 H 6 .cf >N ; \NH 2 X N :CX-CH 3 or by the condensation of aromatic nitriles with acid chlorides in the presence of aluminium chloride (Eitner and Krafft, Ber., 1892, 25, p. 2263). In using benzoyl chloride in this reaction the condensation is found to proceed better if a little ammonium chloride be added :

or H rxro-r H rori _^ C 6 H 6 -C-C1 OC-CeHs 2C,H 6 -CN+C 6 H 6 -C N-C(C,H 6 )-N N-C(C 6 H 6 ):N The cyanidines behave as weak bases.

Mention may be made here of cyanuric acid, HsCjNaOs, which contains the same ring system as the cyanidines. It was first prepared by C. Scheele and is formed when urea is strongly heated or when cyanuric chloride is treated with water. It is usually represented by the inset formula and is closely related to cyanic acid and cyamelide, the relationships existing between the three compounds being shown in the diagram (see also A. Hantzsch, Ber., 1906, 39, p. 139):

HO-C Ordinary temperature Cyanic acid CNOH temperature Cyamelid (CNOH)

Cyanuric acid Decomposes easily C0 2 +NH, Decomposes with difficulty.

Note - this article incorporates content from Encyclopaedia Britannica, Eleventh Edition, (1910-1911)

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