Synthesis of heterocycles. Construction of the 1-azabicyclo[2.2.1]heptyl system by sequential ring-closure of acylic β-ammonio substituted radicals

Article abstract of DOI:10.1016/0040-4039(96)01231-2

Treatment of an irradiated solution of 1-methyl-1-(2-propynyl)-1-bis(2-phenylselenylethyl)ammonium iodide in tert-amyl alcohol with tributyltin hydride is found to be an effective procedure for the synthesis of 1,4-dimethyl-1-azoniabicyclo[2.2.1]heptane iodide. Attachment of a trimethylsilyl or phenyl substituent to the terminal carbon of the triple bond in the alkynyl salt leads to bridgehead-substituted bicylic heterocyclic salts.