800
References
1. Chem. Rev. 1997, 97(2), see entire issue.
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L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. J. Am. Chem. Soc. 1997, 119,
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12. Available from Alltech Associates, Inc., 2051 Waukegan Rd., Deerfield, Il 60015.
13. Experimental details for 5: A mixture of 5-bromonaphthosultam (4, 0.20 g, 0.70 mMol), triphenylphosphine resin (1, 3
mMol/g, 0.58 g, 1.8 mMol) and methanol (45 mg, 1.4 mMol) in dichloromethane (8 mL) was magnetically stirred and
cooled in an ice bath. Di-t-butylazodicarboxylate (DBAD, 2, 0.32 g, 1.4 mMol) was added all at once and stirring continued
for 30 min. The ice bath was removed and trifluoroacetic acid (TFA, 4 mL) was added. After 60 min. The reaction mixture
was filtered (Celite®), the residue washed with DCM (3×10 mL) and the combined filtrate was evaporated to dryness. The
crude product was dissolved in DCM (5 mL) and 1N HCl (2 mL) and filtered through a phase separation tube (8 mL,
hydrophobic). The organic layer filtrate was evaporated to leave a gray solid (0.21 g, 100%). 1H NMR (CDCl3); δ 8.30 (d,
1H, J=8.4 Hz), 8.04 (d, 1H, J=7.2 Hz), 7.87 (dd, 1H, J=8.4 Hz, J=7.2 Hz), 7.78 (d, 1H, J=8.1 Hz), 6.60 (d, 1H, J=8.1 Hz),
3.37 (s, 3H). Positive ESMS m/z=300. Experimental details for 5 using excess 5-bromonaphthosultam: Experiment was run
exactly as above using MeOH as the limiting reagent (20 mg, 0.63 mMol). The gray solid residue obtained after solvent
evaporation was dissolved in DCM (4 mL), placed in a 20 mL scintillation vial, carbonate resin (3.0 mMol/g, 0.12 g, 0.35
mMol) was added, the vial was capped and shaken 16 h. After filtration through a polypropylene frit and DCM wash the
solvent was evaporated to leave a gray solid (0.18 g). Physical data were identical to the sample above. No starting material
was present (1H NMR, HPLC and ESMS).
14. Available from Argonaut Technologies, Inc., 887 Industrial Rd., Ste G, San Carlos, CA 94070.