13772-59-3Relevant articles and documents
The abnormal behavior of an atropisomer: 3,3′-dibromo-1,1′- difluoro-2,2′-binaphthyl reacting with alkyllithium compounds
Leroux, Frederic,Mangano, Giuseppe,Schlosser, Manfred
, p. 5049 - 5054 (2007/10/03)
1-Fluoro-2-(triethylsilyl)naphthalene (1) and other 1-fluoronaphthalenes bearing a metalation-resistant substituent at the 2-position proved to be totally inert toward base attack. 3-Bromo-1-fluoronaphthalene (6), readily prepared from the 2-bromo isomer 5 by deprotonation-triggered heavy halogen migration, was converted into 3,3′-dibromo-1,1′-difluoro-2,2′- binaphthyl (8) by consecutive treatment with lithium diisopropylamide, copper(II) bromide and nitrobenzene. The dilithiated intermediate generated from the atropisomer 8 by treatment with 2 equiv. of butyllithium reacted with a variety of electrophiles to afford products such as the diacid 12 or the bis(phosphanes) 14 and 15 in high yields. The latter compound was also obtained in a straightforward manner from (4-fluoro-2-naphthyl)diphenylphosphane oxide (16). Unexpectedly, neither the 3,3′-dibromobinaphthyl 8 nor its 3,3′-diiodo analogue 18 were amenable to a unilateral but only to a double-sided halogen/metal permutation. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
CYCLOPENTA[B]NAPHTHALENE DERIVATIVES
-
Page/Page column 33-34, (2008/06/13)
The invention relates to cyclopenta[b]naphthalene derivatives of general formula (I), where Z, A, n, R, L5, L6, (II) and (III) have the meanings defined in claim (1), the use thereof in liquid crystal or mesogenous media, liquid crystal or mesogenous media comprising at least one of said cyclopenta[b]naphthalene derivatives and electrooptical display elements comprising said liquid crystal or mesogenous media.