832-80-4Relevant articles and documents
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Meinwald et al.
, p. 4751 (1959)
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Mechanochromism, Twisted/Folded Structure Determination, and Derivatization of (N-Phenylfluorenylidene)acridane
Matsuo, Yutaka,Wang, Ya,Ueno, Hiroshi,Nakagawa, Takafumi,Okada, Hiroshi
supporting information, p. 8762 - 8767 (2019/05/29)
(N-Phenylfluorenylidene)acridane (Ph-FA) compounds with electron-withdrawing and -donating substituents (H, MeO, Ph, NO2, Br, F) at the para position of the phenyl group were successfully synthesized by Barton–Kellogg reactions of N-aryl thioacridones and diazofluorene. By using the substituent on the nitrogen atom to alter the electronic properties, both the folded and twisted conformers of p-NO2-C6H4-FA could be crystallographically characterized, which enabled the charge transfer from the electron-donating acridane moiety to the electron-accepting fluorenylidene moiety to be understood. Ground-state mechanochromism, thermochromism, vapochromism, and proton-induced chromism were demonstrated between the folded and twisted conformations of the conformers. Protonation and chemical oxidation of Ph-FA gave two stable acridinium compounds, namely, the fluorenylacridinium and acridinium radical cations. The present study will contribute to the development of functional dyes and organic semiconductors.
Efficient synthesis of ferrocifens and other ferrocenyl-substituted ethylenes: Via a 'sulfur approach'
Mlostoń, Grzegorz,Hamera-Fa?dyga, Róza,Celeda, Ma?gorzata,Heimgartner, Heinz
, p. 4350 - 4356 (2018/06/21)
Stable and non-odorous alkyl ferrocenyl thioketones react with bis(4-methoxyphenyl)diazomethane according to the 'two-fold extrusion' reaction principles, and tetrasubstituted ethylenes obtained thereby can be demethylated to give (Fc,2OH)-ferrocifens in good yields. The method offers an alternative approach to this class of medically relevant compounds. A similar protocol with alkyl ferrocenyl thioketones and selected diaryldiazomethanes leads to ferrocenyl-substituted ethylenes including dibenzofulvenes. These products are of potential interest for electrochemical and photophysical studies.
New applications of hetaryl thioketones for the synthesis of hetaryl-substituted ethenes via 'two-fold extrusion reaction'
Mlostoń, Grzegorz,Urbaniak, Katarzyna,Pawlak, Aneta,Heimgartner, Heinz
, p. 127 - 139 (2017/03/14)
A series of aryl/hetaryl thioketones was applied for the reactions with aryl/hetaryldiazomethanes yielding, after elimination of N2, the corresponding thiiranes. The relatively unstable dihetaryldiazomethanes were generated in situ from the corresponding hydrazones by oxidation with DMSO. The obtained thiiranes were converted into tetraaryl/hetaryl-substituted ethenes in good yields by desulfurization performed with tris(diethylamino)phosphine ((Et2N)3P).