Naphtho perylene

Naphtho- (naphthalene) Perylo- (perylene) Phenanthro- (phenanthrene)... 

FIGURE 9 Moderately rapid gradient separation. Column XTerra MS C, IS, 4.6x 20mm 3.5p.m. Gradient 0 to 100% B over 4min,A 0.1% formic acid in water, B 0.1% formic acid in acetonitrile. Flow rate 3.0mL/min. Temperature 30°C. Detection UV at 254 nm. Instrument Alliance 2795 with 996 photodiode array detector. Compounds (I) acetanilide, (2) triamcinolone, (3) hydrocortisone, (4) 2-amino-7-chloro-5-oxo-5H-[l]benzopyrano[2,3-b]pyridine-3-carbonitrile, (5) 6a-methyl-17a-hydroxyprogesterone, (6) 3-aminofluoranthene, (7) 2-bromofluorene, (8) perylene, (9) naphtho(2,3-a)pyrene. 

At one point in this 1-ring buildup there are three possible isomers (Figure 2). The 7-ring dibenzo[e,ghi]perylene has three nonequivalent bay regions. A two-carbon addition to each of these will produce three different 8-ring PAHs. Two of these were previously known before this work,benzo[a]coronene and benzo[pqr]naphtho[8,l, 2-bcd]pery lene. The third was not, but a unknown compound was found which almost co eluted in the HPLC with benzo[a]coronene. This was isolated and shown to be the third isomer [5]. This can be taken as a tacit proof of the 1-ring buildup path. 

Retention behavior was compared with a series of planar PAHs pyrene, benzo[ghi]perylene, coronene, benzo[pqr]naphtho[8,l,2-hcd]perylene, naph-tho[8,l,2-ahc]coronene, and ovalene (obtained from Aldrich or by synthesis). 

Naphtho[2,l,8-(jira] naphthacene Naphtho[l,2-f>] triphenylene Ovalene Pentacene Pentaphene Perylene Phenanthrene Phenanthrene, dimethyl-Phenanthrene, methyl-Phenanthrene, tetramethyl-Picene Pyrene... 

PTAD reacts with perylene to provide polycyclic derivative 63, probably via Diels-Alder adduct 62, which is further stabilized by oxidation to the final product (74CB1406). Similar addition of PTAD to naphtho[l,2,3,4-de/]chrysene and other polycyclic arenes has also been described (75CZ92 88CB1647). 

The gas-phase 4- -2-cycloaddition of benzyne with perylene produced naphtho[l,2,3,4- fti]perylene under solvent-free conditions. The microwave-catalysed reaction of A-(2,4-dicyano-l,5-dimethyl-3-phenylcyclopenta-2,4-dienyl) 2,2,2-trifluoroacetamide with alkynes formed bicyclic and polycyclic compounds. The Diels-Alder reaction of maldoxin (67) with an isopropenylallene (68) yielded a cycloadduct (69) closely related to chloropestolide A and a second adduct, which... 

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