Cyanates and Their Thio Derivatives: Volume 2 (1977)

Chapter 17 Syntheses and preparative purposes of isocyanates (pages 619–818): Reinhard Richter and Henri Ulrich
Chapter 18 Syntheses and preparative functions of thiocyanates (pages 819–886): R. G. Guy
Chapter 19 Selenocyanates and comparable 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 workforce (pages 1003–1221): L. Drobnica, P. Kristian and J. Augustin

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Reaction of carbamates (178) with phosphorus pentachloride produces uichlorophosphazenes (179). which eliminate alkyl halide quite readily to produce the isocyanate 180. P(O)NCO + RCI (180) A revised procedure for the synthesis of 180 has appeared recently’”. C=NPX,CI]CI ROCON=PX,CI S = Alkyl. aryl. ArO. CI Also thermolysis of alkyl and arylphosphoryl carbamates (182) can be used to synthesize phosphoryi i s o c y a n a t e ~The ~ ~ ~generated . alcohol or phenol has to be removed in order to prevent recombination.

In these reactions are the corresponding tribenzyl isocyanurates. Infrared spectroscopicz~onitoringof the reactions revealed 17. Syntheses and preparative applications of isocyanates 669 slbw conversion of the initially formed dimers into trimers. Catalysed trimerizations of other aliphatic isocyanates could be shown to proceed in some cases via formation of dimers as intermediates. A related but slow conversion of phenyl isocyanate to triphenyl isocyanurate via 1,3diphenyl-l,3-diazetidinedionewas observed in presence of a guanidine catalyst'*".

Ph,NH + COCI? Ph-,NCOCI (79) Ph,NH + MeNCOT 3 MeNH? c Ph,NCONHMe (78) Reinhnrd Richter and Henri Ulrich 640 Low boiling aliphatic isocyanates are also obtained upon heating of N,N'-dialkylureas with d i p h e n y l ~ a r b o n a t e ~ ~ . , ureas hav$g double b m d s in conjugation to the N H C O N H group) dissociate more readily than N,N'-diarylureas. For example imidazolg substituted ureas (80). N '-ca r bo n y I d i i in id a zo 1e ( 81 ) w i t h p r i ma ry a ni i n es. d i ssoc i a I e c x ceed in g I y readily to the corresponding isocyanate a n d imidazolegO.

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