BASE-CATALYZED ELIMINATION OF PARA-SUBSTITUTED THIOPHENOXIDES FROM 4-(ARYLTHIO)AZETIDIN-2-ONES

Previously we postulated the E 1cBRmechanism for reactions of 4-(aryloxy)azetidin-2-ones in aqueous alkali to give para-substituted phenoxide ions and 3-hydroxyacrylamide oxyanion.1 Rate constants for the nucleofugic step can be obtained using this system, and we anticipated that with appropriate 4-substituted azetidin-2-ones we could rank several nucleofuges and possibly obtain a quantitative structure-activity relationship for them.2 Here we report on the E1cBRreactions of 4-(arylthio)azetidin-2-ones 1–6 in aqueous alkali. © 1990, American Chemical Society. All rights reserved.