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Cycloarenes, a New Class of Aromatic Compounds, III. Studies towards the Synthesis of Cyclo[ d.e.d.e.e.d.e.d.e.e ]decakisbenzene
Author(s) -
Staab Heinz A.,
Diederich François,
Čaplar Vesna
Publication year - 1983
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198319831219
Subject(s) - chemistry , phenanthrene , yield (engineering) , sulfur , extrusion , medicinal chemistry , stereochemistry , organic chemistry , metallurgy , materials science
Attempts to synthesize the cycloarene 2 starting from benzo[ c ]phenanthrene building blocks are reported: From 3 , the preparation of which along different routes is dealt with, bis(bromomethyl) and bis(mercaptomethyl) derivatives 4 and 5 , respectively, were obtained. Cyclisation of 4 and 5 yielded 12 from which by sulfur extrusion the carbocyclic system 14 was prepared. Stevens rearrangement of 12 and subsequent elimination yielded 17 . Scholl reaction of 14 resulted in the formation of 18 by only one‐sided cyclisation. Similarly, photo‐cyclodehydrogenation of 17 did not yield 2 but 19 . – The new helical aromatic systems present in 18 and 19 are discussed on the basis of spectroscopic results.