ELIMINATION OF 2-T-BUTYL-4-DIMETHYLAMINO-1-PHENYLBUTAN-2-OL - MAGNETIC NON-EQUIVALENCE OF A TERTIARY BUTYL GROUP

Acid-catalysed elimination of 2-t-butyl-4-dimethylamino-1-phenylbutan-2-ol and its o-chloro analogue yield ternary mixtures of 2-t-butyl-4-dimethylamino-1-arylbutenes (one but-1- and two but-2-enes). In each case the t-butyl PMR signal of one of the but-2-enes forms a sharp 9 proton singlet while that of the other isomer displays a sharp 6 plus a broad 3 proton singlet. These and other PMR differences are interpreted in terms of probable conformations and allow tentative configurational assignments to bemade. © 1969.