Ethylidene norbornadiene

Ethylene has been co-polymerized with a range of cycloolefms, including cyclobutene,596 cyclopentene,596 cyclohexene,597 norbornene (NB),596 5-phenyl-2-norbornene,598 5-vinyl-2-norbornene,599 5-ethylidene-2-norbornene,600 dimethano-octa-hydro-naphthalene,601 phenyldimethano-octahydro-naphthalene,598 and norbornadiene.602 Several non-conjugated cyclodiolefins have been co-polymerized as well.603... 

TYPICAL COMONOMERS Ethene, propene, ethylidene norbornene (ENB) or dicyclopentadiene or (DCPD), 1,4 hexadiene (4,4 HD), or vinyl norbornene (VNB) or norbornadiene (NBD). - ... 

These three monomers have what appears as a single olefinic resonance in the terpolymers, but, the two norbornadiene types of monomer each show two characteristic resonances. In the methylene noroborene terpolymer, the olefinic resonances arise from two protons, each giving a separate signal whereas in the ethylidene norbonene terpolymers this is only one proton, the signal of which appears as a doublet. In view of these considerations, it is more difficult to detect the olefinic resonance in the latter instance. 

Nitrosyl chloride adds to 5-methylene-2-norbornene (126) and to 5-ethylidene-2-norbornene (lOQ to give dimers of the exo,cis-nitrosochlorides. Similarly, norbornene and norbornadiene add without rearrangement and it is concluded that molecular, and not ionic, addition is important. Addition of deuterium halides to norbornene, and bromine to cyanonorbornenes, has been further studied. With cis,cndo-5,6-dicyanonorbornene mainly cis,exo... 

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