Domino ring-opening metathesis–ring-closing metathesis of bicyclo[2.2.2]octene derivatives: scope and limitations

Abstract

Domino metathesis involving ring-opening metathesis–ring-closing metathesis (ROM–RCM) of a bicyclo[2.2.2]octene derivative having an appropriate alkene chain, expected to produce a 7/6 fused bicyclic system, provided a decalin system in contrast to ROM–RCM of the corresponding bicyclo[2.2.1]heptene analogues, which as expected produced the 7/5 fused bicycles. The expected 6/7 bicyclic system could, however, be made through RCM of the elusive ROM product prepared from the same bicyclo[2.2.2]octene analogue by a nonmetathetic route. A rationale to explain the difference in reactivity pattern between these two systems toward ROM–RCM has been forwarded.