SYNTHESIS AND REACTIONS OF THE STEREOISOMERS OF TETRABENZO(A,C,G,I)CYCLODODECENE AND TETRANAPHTHO[A,C,G,I]CYCLODODECENE

Starting with the bis-mercaptane 2 and the dibromide 3 (E,E)-tetrabenzo[a,c,g,i]cyclododecene (1a) and the Z,Z isomer 1b are stereoselectively synthesized via the racemic (a) and the meso form (b) of the bis-thioether 4 and the disulfone 5. Acid-catalysed rearrangement of 1a an 1b leads to the isomeric phenanthro[9,10-a]fluoranthene derivatives 7a and 7b. Racemate, meso form, and the optically active (-)-SS form of the tetranaphtho compound 18 are synthesized according to 1a and 1b from racemic or optically active starting materials 14 and 15.