NOVEL PHASE-TRANSFER CATALYST CAPABLE OF FACILITATING ACID-CATALYZED AND-OR ELECTROPHILIC REACTIONS

Since the beginning of the 1970s, phase transfer catalysis (PTC)1,2has rapidly developed as a synthetic technique. In-deed, the development of and the interest in PTC is as wide-spread in industrial circles as in the academia. The general utility and advantages of PTC are well documented.3-7All known phase transfer catalysts have two properties in common: (1) they contain hydrophobic alkyl or aryl groups; (2) they are only able to transfer anionic reagents to (or into) organic solvents.8,9Consequently the usefulness of PTC is limited to reactions involving anions (i.e., nucleophilic or base-mediated reactions). In this communication an acid-catalyzed hydrolysis, using the first reported —negatively charged– phase transfer catalyst, is described.10It is believed that this and other analogous phase transfer catalysts will greatly expand the usefulness of PTC, as acid-mediated and/or electrophilic reactions can be done for the first time via this technique. © 1979, American Chemical Society. All rights reserved.