NEW FRIEDEL-CRAFTS CHEMISTRY .19. CYCLIALKYLATIONS OF SOME PHENYLALKANOLS

Tertiary 3- and 4-phenylalkanols underwent cyclialkylation readily at room temperature with sulfuric acid to yield the corresponding indans and tetralins. Primary and (ordinary) secondary 3-phenylalkanols did not undergo cyclialkylation even at high temperature with phosphoric acid; 1,3-diphenyl-1-propanol cyclized readily. 3-Methyl-3-phenyl-1-butanol was dehydrated (mainly) by phosphoric acid at 230°, but some cyclialkylation occurred. The requirement of a stable secondary or tertiary carbonium-ion intermediate is implied by these results; in the case of the last example, a 1,3-phenyl shift provides the required intermediate. © 1969, American Chemical Society. All rights reserved.