A steric butress was used to initiate an intramolecular Diels-Alder cycloaddition recation. Furfurylamine and 4-bromo-1-butene were made to react to produce N-butenylfurfurylamine which acted as a precursor for the reaction. A steric butress trityl chloride was added to N-butenylfurfurylamine followed by heating under replux in toluene in order to obtain the final Diels-Alder cycloadduct The buttress was then removed by hydrolysis to yield the Diels-Alder cycloadduct, 9-aza-1,4-oxidobicyclo[4.4.0]dec-2-ene. A separate experiment was performed to observe if N-butenylfurfurylamine was able to from the desired Diels-Alder cycloadduct without a steric buttress.

Assessing the need for a trityl group as a steric buttress to initiate a Diels-Alder reaction

249th National Meeting (2015)

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