Acetyl cyanide acetylenes

Considerable variation is also possible in the carbonyl function, and in addition to simple aldehydes and ketones, acetyl cyanide,292 diethyl oxomalonate,293 diethyl oxalate,294 and ethyl cyanoformate 295 [Eq. (77)] will all undergo cycloaddition to alkenes to form the corresponding oxetanes. Oxetanes are also formed in certain circumstances from both a,j8-unsaturated aldehydes298 and acetylenic ketones.297... 

Acrolein Acetyl chloride Acetylene-arsenic trichloride Acetyl fluoride Aluminum chloride Aluminum arsenide Ammonium cyanide... 

Synthesis. - Type A Syntheses (S-C H -N + C). The C-nucleoside (182) is formed by condensation of 2-amino-4-chlorobenzenethiol with an acetylated aldonic nitrile or glycosyl cyanide followed by deacetylation23. 2-Aminobenzenethiol reacts with RC0CsCPh(Rs2-thienyl) to give (183). The latter cyclises to 2-phenylbenzo-thiazole on attempted recrystallisation (MeOH). With terminal acetylenic ketones a mixture of benzothlazolines results232. 

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