Oxygen → Tetraphenylethylene

Participants

Reaction Steps

N,N'-Bisbenzyl spirodiamide 11 was obtained by diethyl ether extraction from the brine-DMSO reaction mixture in 80-93% yield. Bulkier derivatives N,N'-bis(diphenylmethyl)-spirodiamide 12 and N,N'-bis(9-anthracenylmethyl)-spirodiamide 13 have also been synthesized from diphenymethyl chloride and 9-anthracenylmethyl chloride, respectively. N,N'-bis(9-anthracenylmethyl)spirodiamide 13 was synthesized using the same method as bisbenzyl derivative 11 and isolated by column chromatography in 35% yield. The anthracenyl group in 13 is sensitive to oxygen, so analytically pure crystalline product was collected directly from fractions by cooling the chromatography fractions in a refrigerator under nitrogen. Diphenylmethyl chloride itself reacted with the basic equilibrium mixture of sodium methylsulfinylcarbanion and spirodiamide dianion in DMSO to produce a fluorescent product, tetraphenylethene. By employing a 100% excess of diphenylmethyl chloride, N,N'-bis(diphenylmethyl)-spirodiamide 12 was isolated by column chromatography in 22% yield.

Provenance & Evidence