Ethyl 3-Phenylpropenate

Phenylpropenal reacted with ethylamine in the presence hydrogen and Pt as catalyst and BaS04 and N-ethyl-3,3 -diphenyldipropylamine (alverine) was obtained. 

Iodorhodium(IIl) porphyrins also efficiently catalyze the reaction of ethyl diazoacetate with simple alkenes. generally providing the cw-isomers as the major product77 79110. The cis( tram ratio increases when bulkier porphyrins, such as tetramesitylporphyrin (TMP), are employed. The mechanism of this rhodium-catalyzed cyclopropanation with diazoacetate is interpreted as proceeding via carbene complexes79 80 111,112. Based on these results, asymmetric cyclopropanation of alkenes with ethyl diazoacetate is achieved if catalyzed by a chiral wall porphyrin81. An earlier described binaphthyl-system of this type82113114, introduced as an iodorhodium(lll) complex, 6, forms an extremely active catalyst and leads to m-cyclopropanes (preferred over the rran.v-products) with moderate to poor enantioselectivities if styrene, 1- and 3-phenylpropene are used as substrates (10-60% ee)81. 

Photocycloaddition of 2-methyl- and 2-ethyl-naphthoquinone to styrene yields three cyclobutane products (457,458) in which the 8-phenylisomer dominated. " The ratio of 7-phenyl to 8-phenyl products was 1 6 for the methylquinone and 1 3.5 for the ethyl derivative. The authors suggest that in these examples dipole-dipole interactions overcome any adverse repulsions. Changes in the olefin brings about changes in the ratio of products. Thus with 2-phenylpropene the ratio... 

Arnold and Smolinsky determined that the pyrolysis of 3-deuterio-3-ethyl-6-phenyl-5-hexen-3-ol (48) produced 3-deuterio-3-phenylpropene (49) and 2-pentanone (50). This result confirmed a syn elimination and suggested a cyclic transition structure for the reaction (equation 10.77). ... 

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