Oxygen → Tetraphenylethylene

HRID 653804

反応式

HRID 653804 の反応式
[C:1]1([CH:7](Cl)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15]1[C:28]2[C:19](=[CH:20][C:21]3[C:26](C=2CCl)=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:17][CH:16]=1.O=O>>[C:1]1([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:20]([C:19]2[CH:28]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 3

HCID 977OxygenHCID 7035ChlorodiphenylmethaneHCID 323859-(Chloromethyl)anthracene

生成物 1

HCID 69437Tetraphenylethylene

実験手順

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.

後処理

  1. customisolated by column chromatography in 35% yield
  2. customwas collected directly from fractions
  3. temperatureby cooling the chromatography fractions in a refrigerator under nitrogen
  4. customDiphenylmethyl chloride itself reacted with the basic equilibrium mixture of sodium methylsulfinylcarbanion and spirodiamide dianion in DMSO

出典と根拠

ORDレコード
ord-e1d2da41bdb046d9bb5aa1a16b2dd3e5
出典データセット
uspto-grants-1992_07
特許番号
US05128466

関連ノート

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