Methylterrylene isomers

Arenium cation or radical cation? An insight into the cyclodehydrogenation reaction of 2-substituted binaphthyls mediated by Lewis acids

“…Substrate 3 has a melting point of 109-110 C and decomposes at 125-127 C. 33 For this reason, milder Scholl reaction conditions were assayed with this substrate. 19 A solution of AlCl 3 in dry chlorobenzene at 80 C was used to promote the reaction (entry 5, Table 1); however, no intramolecular cyclization product was observed and 2-methoxynaphthalene was obtained as major product, due to the C1-C1 0 bond cleavage of the substrate. Some minor products from coupling between naphthyl group and chlorobenzene, homocoupling of chlorobenzene and other chlorinated compounds were detected by GC-MS.…”

“…One of the postulated mechanisms is known as the Scholl reaction, that proceeds through the formation of an electrophilic complex or s-complex (shown as H + for simplicity in Scheme 2, but it could also be a s-complex formed with a Lewis acid). 18 Usually, methodologies related to this mechanism involve the use of strong Lewis acids such as AlCl 3 dissolved in chlorobenzene, 19 complexes of fused salts such as AlCl 3 /NaCl 20 or AlCl 3 /SO 2 , 21 among others. 15 In contrast, the other proposed mechanism for the reactions mediated by Lewis acids is the oxidative aromatic coupling.…”

Oxidative cyclodehydrogenation of a perylene derivative: different reagents give different products

“…10 Compound 2 possesses an intense fluorescence with a small Stoke shift (10 nm) as expected for a rigid molecule (Fig. † Furthermore, the DCI-CH 4 TOF MS CI + spectrum showed a peak at 394.1167 for C 30 H 15 F [M] + , confirming the cyclodehydrogenation reaction.…”

“…2). FeCl 3 ,9f,g,r,10,16a,b CuCl 2 or Cu(OTf) 2 and AlCl 3 , 9a,c,r,10 Tl(O 2 CCF 3 ) 3 in CF 3 CO 2 H or BF 3 ÁOEt 2 , 9o Pb(OAc) 4 /BF 3 ÁEt 2 O in MeCN, 9n triethyloxonium hexachloroantimonate (Et 3 O + SbCl 6 À ), 16c,d SbCl 5 , 16e-g MoCl 5 , 9h-j,16h etc.) Recently Rathore et al 15 demonstrated that the DDQ/H + oxidation system (which is known to oxidize a variety of electron donors with oxidation potential as high as B1.7 V to the corresponding cation radicals) can be effectively employed for a variety of oxidative cyclodehydrogenation reactions.…”

Design and synthesis of aromatic molecules for probing electric fields at the nanoscale

“…19 The synthetic route started with the preparation of 2-(4-uoronaphthalen-1-yl)-4,4,5,5tetramethyl-1,3,2-dioxaborolane 2, which was obtained in 58% yield by Miyaura borylation of 1-bromo-4-uoronaphthalene 1, using a modied procedure to that reported by Miyaura et al 20 3-Bromoperylene 4 was obtained in 87% yield by NBS bromination of perylene 3, following the procedure reported by Mitchell et al 21,22 in combination with our previously reported method. 23 Subjecting 2-(4-uoronaphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2 with 3-bromoperylene 4 to modied Suzuki cross-coupling conditions 23,24 afforded the key intermediate 3-(4-uoronaphthalen-1-yl)perylene 5 in 75% yield. The structure of 5 was conrmed by 1 H, 13 C and 19 F NMR spectroscopy, and by UV and mass spectrometry.…”