trans-Cycloalkenes. Part VI. Addition of iodine(I) azide to trans-cyclo-octene

Abstract

Addition of iodine(I) azide to trans-cyclo-octene gave trans-1-azido-4-iodocyclo-octane (VI) as major product together with small amounts of 5-azidocyclo-octene (I) and 1-(4-iodocyclo-octyl)-5-methyltetrazole (II). Transannular rearrangement with 1,5-hydrogen shift is thus considered to be the predominant reaction pathway. The key information required for an assignment of structure to compound (VI) was provided by preparation of the labelled analogue from [1,2-²H₂]-trans-cyclo-octene. Both cis- and trans-1-methylcyclo-octene gave cis-cyclo-octenylmethyl azide on treatment with iodine azide.