155386-57-5Relevant articles and documents
Electrophilic substitution of 7-tert-butyl-1-substituted pyrenes. A new route for the preparation of 1,3-disubstituted pyrenes
Yamato, Takehiko,Fujimoto, Masakazu,Nagano, Yoshiaki,Miyazawa, Akira,Tashiro, Masashi
, p. 321 - 330 (1997)
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Medium-Sized Cyclophanes. Part 31. Synthesis and Electrophilic Substitution of 8-Substituted Metacyclo(1,3)pyrenophanes
Yamato, Takehiko,Miyazawa, Akira,Tashiro, Masashi
, p. 3127 - 3138 (2007/10/02)
syn- and anti-2,11-Dithiametacyclo(1,3)pyrenophanes 15 have been obtained by coupling the corresponding 1,3-bis(bromomethyl)pyrene 11 and 1,3-bis(mercaptomethyl)benzenes 14 in ethanol under high-dilution conditions.Oxidation of the obtained thiametacyclophanes 15 with m-chloroperbenzoic acid afforded the corresponding syn- and anti-disulfones 18.Pyrolysis of the syn- and anti-disulfones 18 afforded exclusively the corresponding anti-metacyclo(1,3)pyrenophane 19 in 40-70percent yield along with the ring-cleavage product, 7-tert-butyl-1,3-dimethylpyrene 8.The nitration of 5,15-di-tert-butyl-8-methyl- 19b and 5,15-di-tert-butyl-8-methoxy-metacyclo(1,3)pyrenophane 19d with 1 mol equiv. of copper(II) nitrate in acetic anhydride solution exclusively occured on the more reactive pyrene ring to afford 14-nitro derivatives 21a and 21b in 83 and 86percent yield, respectively.On the other hand, the bromination of substrates 19 with bromide in methylene dichloride solution afforded 13-bromo derivatives 23 along with the transannular cyclization products 24 and 25.These different orientations for the electrophilic substitution are also discussed.