| Abstract
| - Syntheses of 5-isopropyl-1,3-cyclohexadiene andsyn-5-isopropyl-2,3-dioxabicyclo[2.2.2]octane,byroutes that would allow completely diastereoselective introduction ofdeuterium labels, are described.The reaction of the isopropyl cyclohexadiene with singlet oxygenis shown to give an endoperoxidethat is derived by preferential attack on the more sterically hinderedface of the diene. A possiblemechanistic explanation of this result is that the attack from the lesshindered face leads to “ene”reaction rather than endoperoxide formation. However, thismechanism would require that the“ene” reaction and cycloaddition proceed via a commonintermediatepresumably a perepoxide.
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