PYROLYSIS OF TRANS-CINNAMIC ACID SODIUM TRANS-CINNAMATE STYRENE DISTYRYL AND CIS- AND TRANS-STILBENE . PRODUCTS AND IMPLICATIONS

The title compounds were each pyrolyzed at temperatures ranging from 500 to 900°, and the resulting products and their distributions were determined. Pyrolysates from cinnamic acid and sodium cinnamate comprised chiefly styrene, trans-stilbene, phenylnaphthalene, phenanthrene and toluene. Styrene, relatively stable under the pyrolytic conditions, did not likely undergo secondary decomposition in the pathway from cinnamic acid to products. Distyryl was converted mainly into 1-phenylnaphthalene, 2-phenylnaphthalene, naphthalene, and, at higher temperatures, into fluoranthene. Pyrolysis of cis- and trans-stibene resulted in production of phenanthrene and thermal cis-trans isomerization, in addition to the formation of a variety of other products. The numerous products generally obtained and their distributions suggest a multiplicity of mechanistic pathways involving nonfree radical, as well as free radical, intermediates. © 1969, American Chemical Society. All rights reserved.