5-Alkenyl and 5-alkylidene-norbornene-2 cpds - novel multi-stage process from cyclopentadiene or dicyclopentadiene

摘要

Prepg. 5-alkylidene and/or 5-alkenyl-norbornene-2-cpds. of formula (I) or (II) (where R1,R2 and R3 are H or alkyl) are prod. by (a) forming the 5-hydroxyalkyl cpd. (III) above from cyclopentadiene and/or dicyclopentadiene, pref. by reacting with a dialkyl alkenyl carbinal ester at 100-190 degrees C followed by alkaline hydrolysis of the prod. at 130-170 degrees C (b) reacting (III) with a cpd. R4SO2Cl(where R4 is aliphatic or aromatic) in the presence of an organic base pref. pyridine, picolines, lutidines, trimethylamino or dimethylaniline, to form the sulphoester (c) eliminating the sulphoester gp. using an org. base, pref. pyridine, picolines, lutidines, dimethylamine or triethylamine, in a polar solvent, pref. dimethylformaide, dimethylacetamide, hexametapel or alcohols, at at 50-150 degrees C. Alternatively the alcohol plus alcoholate may be used as solvent/base and also the sulphoester may pref. not be isolated (d) sepg. (I) and nII) formed pref. by distillation (e) isomerising the 5-alkenyl cpd (II) to the alkylidene (I). The 5-alkylidene cpds. are used as diene monomers in EPDM terpolymers (ethylene/propylene/diene monomers). The process gives higher yields, partic. in step (a) and also avoids costly inters.