A Simple Synthesis of EXO-Tricyclo[3.3.1.0^2,4]non-6-ene

Abstract

Samples of exo-tricyclo[3.3.1.0^2,4]non-6-ene (3) have been frequently required for physical-organic studies and for product comparison purposes in rearrangemtnt studies.^1–3 The compound has been prepared in four steps from norbornadience in less than 5% yield.¹ It has also been prepared from vinylcyclohexene in three steps, along with a variety of by-products, in less than 10% yield.² We report here a simple, clean synthesis of 3 from nor-bornadiene with an overall yield of 45–55%. Additionally, we are reporting the first¹³C NMR spectrum of this compound which will allow for its easy identification in the future.