SYNTHESIS AND CHEMISTRY OF SOME ORTHO-ESTERS OF BICYCLO[2.2.1]HEPTANEDIOLS

Orthoesters have been prepared from cts, exo-2, 3-bornanediol, cis, exo-2, 3-norbornanediol, and cis, endo-2, 3-norbornanediol. Under a variety of conditions, dioxolenium ions were generated therefrom, e.g. hot trifluoracetic acid, acetyl chloride in acetone, hot phenyl isocyanate. The ions did not rearrange under any of the conditions tried, but acetone and cyclohexanone were alkylated by them. Further, the formation of bornylene or norbornene was the result of heating the orthoesters in phenyl isocyanate. © 1979, American Chemical Society. All rights reserved. © 1979, American Chemical Society. All rights reserved.