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Gekoppelte Polycyclen: Synthese, Struktur und Isomerisierung von 1,1′‐Bihomocuban
Author(s) -
Schäfer Jörg,
Polborn Kurt,
Szeimies Günter
Publication year - 1988
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.19881211230
Subject(s) - chemistry , isomerization , medicinal chemistry , cuprate , lithium (medication) , yield (engineering) , bromine , stereochemistry , catalysis , organic chemistry , medicine , physics , materials science , optoelectronics , doping , metallurgy , endocrinology
Coupled Polycyles: Synthesis, Structure, and Isomerization of 1,1′‐Bihomocubane 1,1′‐Bihomocubane ( 1 ) was obtained in 45% yield from 1‐bromohomocubane by lithium–bromine exchange with tert ‐butyllithium, formation of the corresponding lithium cuprate by addition of complex 3 , and oxidation of the cuprate with nitrobenzene. 1 was converted into 1,1′‐binorsnoutane ( 6 ) by means of silver(I) catalysis. The X‐ray structure of 1 showed a short C 1 –C 1 bond (1.460 Å), in accordance with predictions by Ermer and Lex.