Bicyclo octene conjugation

Sulfur-Containing Conjugated n-Systems Annelated with Bicyclo[2.2.2]octene Frameworks... 

Synthesis and properties of cationic -conjugated systems stabilized by bicyclo[2.2.2]octene units including annulated silatropilium ion, thiophene, 1,2-dithiine, 1,4-dithiine, and oligothiophenes 05SL187. 

An enzymatic approach has been advocated for the single-step preparation of small quantities of enantiomerically enriched 2-oxynorbomanes and 2-oxybicyclo[3,2,l]-octanes. Thus, for example, horse fiver alcohol dehydrogenase-catalysed oxido-reduction of ( )-2-norbornanone results in the production of (—)-(lR,4S)-2-nor-bornanone and (-f)-(lS,21, 4R)-endo-2-norbomanol of up to 46 and 66% optical purity respectively. The space-conjugated olefinic double bonds in various nor-bornene and bicyclo[2,2,2]octene derivatives are rapidly reduced by lithium in liquid ammonia benzonorbomadiene, for example, is reduced to benzonorbomane. ... 

Hatanaka and coworkers [28] developed an intramolecular cycloaddition route of 4-alkenylfulvene 115 to give the bicyclo[3.3.0]octene derivative 118 (Scheme 7.27). Treatment of the ynone 113 with 2-ethoxyallyhdenetriphenylphosphorane 114 in THF afforded a mixture of Z-fulvene and -fulvene isomers 115. The fulvenes are formed via initial conjugate addition of the phosphorane to the... 

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