ABSTRACT

Under these conditions the intermediate phosphonate (V) hydrolyzes about 105 times faster than phosphorous acid triesters IV (49). This is because the intermediate phosphorous acid diesters (V) can be ionized under the influence of a base such as OH-to a dimethyl phosphite anion (XI). Westheimer et al. propose a general acid-catalyzed decomposition of this anion under release of an unstable metaphosphite (XII), which rapidly reacts with water to give the anion of the phosphonous acid monoester (X) (49).