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. 2004 Sep 1;101(37):13578–13583. doi: 10.1073/pnas.0402838101

Table 1. Proton NMR data for PPBF and methylated analogs.

Designation R a [6H] b [2H] c [3H] d [3H] e [3H] f [3H] Aromatic graphic file with name zpq03504584200e1.jpg
PPBF NA 1.49 2.95 2.56 2.33 2.14 NA Complex [5H]
4-methyl PPBF para-CH3 1.49 2.96 2.56 2.30 2.14 2.34 7.07, 6.91 [4H]
3-methyl PPBF meta-CH3 1.49 2.96 2.57 2.31 2.14 2.36 7.15, 7.03, 6.92, 6.78
2-methyl PPBF ortho-CH3 1.50 2.98 2.57 2.31 2.15 2.36 7.23, 7.13, 7.05, 6.76

1H chemical shifts (ppm) for PPBF analogs were measured in deuterated chlorofom at 24.8°C. The spectrum of PPBF was characterized by the appearance of signals consistent with the 2,2,4,6,7-pentamethyl-dihydrobenzofuran nucleus linked to an isolated and otherwise unsubstituted phenyl ring. In particular, there was a resonance for the pair of 2,2 methyl groups (1.49 ppm; singlet; 6H), three additional resonances for the 4-, 6-, and 7-methyl groups (2.56, 2.33, 2.14 ppm; singlets; 3 × 3H) and a complex multiplet of aromatic signals (7.02-7.35 ppm) partially obscured by the residual CHCl3 resonance at 7.26 ppm, consistent with the isolated phenyl ring. NA, not applicable. R refers to the position at any methyl substitutions on the phenyl ring.