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Neue extrem deformierte (Biphenylen‐)Kohlenwasserstoff‐Gerüste
Author(s) -
Schulz Jochen E.,
Rissanen Kari,
Vögtle Fritz
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921251011
Subject(s) - chemistry , hydrocarbon , biphenylene , molecule , bond length , isocyanide , carbon skeleton , carbon fibers , medicinal chemistry , stereochemistry , organic chemistry , materials science , composite material , phenylene , composite number , polymer
New Extremely Deformed (Biphenylene)Hydrocarbon Skeletons The tetracyclic carbon skeleton 2‐oxo[3](1,8)biphenylenophane ( 4 ) was synthesized by cyclization of a mixture of the bis(bromomethyl) compounds 7a, b with p ‐tolylsulfonylmethyl isocyanide. 2‐Hydroxy[3](1,8)biphenylenophane ( 5 ) and the [3](1,8)biphenylenophane hydrocarbon 6 were obtained by reduction of 4 with LiAlH 4 and NaBH 4 , respectively. X‐ray analyses of 4 and 6 illustrate the dramatic deformation of bond lengths and angles in these molecules.