Synthesis and protonation studies of syn- and anti-2,4-bishomotropone. Comparison with the behavior of epimeric 2,4-bishomocycloheptatrienols under long- and short-lived ionization conditions

Abstract

Ausgehend von den Verbindungen (I) bzw. (IV) werden das anti‐(II) bzw. syn‐Bis‐homotropon (V) sowie die epimeren Alkohole (IIIa) und (IIIb) AI O 0190 bzw. (VIa) und (VIb) dargestellt.

Synthesis and reducibility of homo-2-methoxyazocines and their benzo-fused derivatives. An examination of heteroatomic influences on the possible generation of 9C-10.pi. homoaromatic dianions

“…As with either 10 or 11, the onset of reduction occurred at approximately -2.8 V, the wave rising continuously into the electrolyte decomposition wave with no observable inflection point. The reducibility of dibenzo derivative 31 compared closely with that of 18 (Ey2 = -3.00 V, = 1-2). A comparison of the electrochemistry of the homo-2methoxyazocines and their benzologues with that of the corresponding azocines discloses a reactivity pattern akin to that exhibited by 1 and benzobicyclo[6.1.0] nonatriene relative to the parent cyclooctatetraenes.…”

“…1 l,12-Homo-6-methoxydibenz[h,f]azoeine (31). A solution of lactam 30 (900 mg, 3.8 mmol) and trimethyloxonium tetrafluoroborate (900 mg, 6.06 mmol) in dry methylene chloride (20 mL) was stirred under nitrogen at room temperature for 20 h. This solution was treated with 1.0 g of sodium bicarbonate dissolved in 25 mL of water.…”