Chapter 17 Syntheses and preparative functions of isocyanates (pages 619–818): Reinhard Richter and Henri Ulrich
Chapter 18 Syntheses and preparative purposes of thiocyanates (pages 819–886): R. G. Guy
Chapter 19 Selenocyanates and similar compounds (pages 887–922): E. Bulka
Chapter 20 organic formation and reactions of cyanates (pages 923–967): Sasson Cohen and Edna Oppenheimer
Chapter 21 Syntheses and reactions of isocyanide dilhalides (pages 969–1001): Henri Ulrich and Reinhard Richter
Chapter 22 The chemistry of the — NCS team (pages 1003–1221): L. Drobnica, P. Kristian and J. Augustin
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Additional info for Cyanates and Their Thio Derivatives: Volume 2 (1977)
I n contrast only dimeric species X,NCONCO were isolated even at - 80°C when this reaction was extended to chlorine and In 1966 Nachbaur and Gottardi reported the synthesis of monomeric ctiloro isocyanate by pyrolysis of its cyclic trinicr. N-trictiloroisocyanuric acid”’. 5 C. and spectral data and derived reaction products verify thc proposed structure. I n the liquid phase chloro isocyanatc undergoes rapid dinierimtion2*’, and on attemptcd distillation extensivc dccornposition occurs. I n contrast iodo isocyanate is relatively stable in ethereal solution.
6 . Miscellaneous methods Carbonimidoyl dichlorides (isocyanide dichlorides) which are available by a variety of synthetic procedures not involving isocyanates as starting materials, are readily hydrolysed to produce isocyanates. The hydrolysis can be conducted with methanesulphonic acid'41, phosphoryl chloride and ~ a t e r ' ~anhydrides'"' ', or formic a ~ i d ' " ~ . RN=CCI, + HCOOH ___* RNCO + CO + 2 HCI Trifluoromethylcarbonimidoyl difluoride (1 14) can be hydrolysed with water to give trifluoromethyl isocyanate ( 1 15)lJ4.
Hexaalkyl phosphortriamides, and bis-Ndialkyl phosphoramidous acid ethyl ester355, as well as a number of amines (pyridines. '. 3-dinzetidinedionc and not the equally possible iminoovazitidinone form. natcs has been discusscd c ~ t e n s i v e l yand ~ ~ i t is assumed that polar internicdiatcs of various chain length arc formed from catalyst and isocyanate. Attack by the catalyst on thc ccntral carbon atom of the isocyanate moiety is believed to be the initial reaction step. 668 Reinhard Richter a n d Henri Ulrich Dimers of isocyanates 0 Monomer Type of Reaction [2 RNCO + Product Aryl.
Cyanates and Their Thio Derivatives: Volume 2 (1977)