OXYMERCURATION-DEMERCURATION OF 7-SUBSTITUTED NORBORNENES AND NORBORNADIENES

The oxymercuration-demercuration of syn- and anti-7-hydroxy- and -acetoxynorbornenes gave high yields of exo,syn- and ezo,anti-2,7-dihydroxynorbornanes, respectively. 7-Acetoxynorbornadiene was converted into a mixture of ezo,syn-2,7-dihydroxynorbornene-5 and endo,endo-3,5-dihydroxynortricycIene. 7-Hydroxynorbornadiene experienced an oxidative rearrangement to yield benzaldehyde as the sole reaction product. The synthetic utility and mechanistic implications of these reactions are discussed. © 1968, American Chemical Society. All rights reserved.