Abstract
An efficient synthesis of 9,10‐dihydro‐9,10‐(methaniminomethano)anthracene and several N‐protected derivatives is described via the double reductive amination of cis‐9,10‐dihydro‐9,10‐dicarboxaldehyde.
Acknowledgments
We thank Bristol‐Myers Squibb for a fellowship for P. Stoy, the National Science Foundation for a REU undergraduate fellowship (CHE 0097585) for J. Rush, and the National Institutes of Health for funding (GM 52491).
Notes
aProcedure for deactivating silica gel: Silica gel (60 Å) was dispersed in a 4:1 mixture of hexanes and hexamethyldisilazane (HMDS) and the resulting slurry added to a chromatography column. The column was washed thoroughly with 4:1 hexanes/ethyl acetate, then again washed thoroughly with hexanes prior to loading the sample onto the column.
bThe 1H NMR spectra for compounds 6 and 7 in CDCl3 have recently been reported (see Refs. 9 and 25), but without 1H‐1H coupling constants or mention of the spectrometer field strength.