Olefin metathesis of syn,syn-2,4,6-triallyl-hexahydro-1,3,5-tripropionyl-s-triazine and nitrolysis products

Abstract

Ring closing olefin metathesis of syn,syn-2,4,6-triallyl-hexahydro-1,3,5-tripropionyl-s-triazine gave an intramolecular cyclized product and an intra/intermolecular dimerized product depending on the choice of organometallic ruthenium catalyst. The intramolecular cyclized product was further reduced and then reacted under nitrolysis conditions with trifluoroacetyl nitrate to give endo-8-(1-propyl)-7,9,10-trinitro-7,9,10-triazabicyclo[4.3.1]decane in 25% yield.

Keywords

• Olefin metathesis
• Ruthenium
• Nitrolysis
• 1,3,5-triazine
• Reduction