len es ▁without ▁bul ky ▁subst itu ents ▁tend ▁to ▁dim er ize ▁in ▁one ▁of ▁two ▁modes . ▁Below , ▁the ▁re actions ▁of ▁stabil ized ▁pl um by len es ▁( at ▁least ▁at ▁the ▁temper atures ▁at ▁which ▁they ▁were ▁studied ) ▁are ▁listed . ▁ ▁Lewis ▁acid - base ▁ad duct ▁formation ▁ ▁Pl um by len es ▁are ▁Lewis ▁acid ic ▁via ▁the ▁vac ant ▁ 6 p ▁orb ital ▁and ▁tend ▁to ▁form ▁ad duct s ▁with ▁Lewis ▁bases , ▁such ▁as ▁trim eth yl am ine ▁N - ox ide ▁( Me 3 NO ), ▁ 1 - az ido ad am ant ane ▁( Ad N 3 ), ▁and ▁mes ity l ▁az ide ▁( M es N 3 ). ▁In ▁contrast , ▁the ▁reaction ▁between ▁st anny len es ▁and ▁Me 3 NO ▁produces ▁the ▁corresponding ▁dist ann ox ane ▁( from ▁ox id ation ▁of ▁Sn ( II ) ▁to ▁Sn ( IV )) ▁instead ▁of ▁the ▁Lewis ▁ad duct , ▁which ▁can ▁be ▁attributed ▁to ▁tin ▁being ▁a ▁period ▁above ▁P b , ▁experien cing ▁the ▁in ert ▁pair ▁effect ▁to ▁a ▁less er ▁degree ▁and ▁hence ▁having ▁a ▁higher ▁sus cept ibility ▁to ▁ox id ation . ▁ ▁In ▁the ▁case ▁of ▁Ad N 3 , ▁the ▁terminal ▁N ▁of ▁the ▁az ido ad am ant ane ▁bind s ▁to ▁the ▁pl um by l ene ▁via ▁a ▁brid ging ▁mode ▁between ▁the ▁Lewis ▁acid ic ▁P b ▁and ▁the ▁Lewis