2-tert-butyl-3-(9-fluorenyl)-2-phenylaziridine | 136175-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-tert-butyl-3-(9-fluorenyl)-2-phenylaziridine
• 英文别名: 2-tert-butyl-3-(9H-fluoren-9-yl)-2-phenylaziridine
• CAS: 136175-28-5
• 化学式: C₂₅H₂₅N
• 分子量: 339.48
• InChiKey: RUQNPLXUMOICCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  21.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  芴 、 2-benzyl-2-tert-butyl-1-(4-p-tolylsulfonyl)aziridine 在 正丁基锂 作用下， 生成 (+/-)-1-(9-芴)乙醇 、 2-tert-butyl-3-(9-fluorenyl)-2-phenylaziridine
  参考文献：
  名称：

  Nitrogen-sulfur cleavage is faster than homolytic ring opening in single-electron transfer to some N-sulfonylaziridines. Competition between SN2 and SET

  摘要：

  The radical anions of the N-sulfonylaziridines, 1a,b and 3 undergo N-S cleavage in place of homolytic ring opening as is demonstrated by reactions with anthracenide A.- Nucleophilic ring opening of the sulfonylaziridines 1a,b and 3 by the carbanions AH-,X-, and Fl- of dihydroanthracene, xanthene, and fluorene, respectively, proceeds with the expected regioselectivity and is slow enough to allow some competition by a single-electron transfer (SET) initiated N-S cleavage, which provides the desulfonated aziridines and bixanthenyl X-X or bifluorenyl Fl-Fl, respectively. The SET path is favored by light. The competition is in favor of SET to the exclusion of the nucleophilic opening when trityl anion reacts with 1a. The twice-found byproducts 11 and 12 require the azirine intermediate 15, which is, at least formally, generated by elimination of TsH from 1a in a non-SET reaction.

  DOI：

  10.1021/jo00024a028

文献信息

• Nitrogen-sulfur cleavage is faster than homolytic ring opening in single-electron transfer to some N-sulfonylaziridines. Competition between SN2 and SET
  作者：Konstantinos Bellos、Helmut Stamm、Dieter Speth

  DOI：10.1021/jo00024a028

  日期：1991.11

  The radical anions of the N-sulfonylaziridines, 1a,b and 3 undergo N-S cleavage in place of homolytic ring opening as is demonstrated by reactions with anthracenide A.- Nucleophilic ring opening of the sulfonylaziridines 1a,b and 3 by the carbanions AH-,X-, and Fl- of dihydroanthracene, xanthene, and fluorene, respectively, proceeds with the expected regioselectivity and is slow enough to allow some competition by a single-electron transfer (SET) initiated N-S cleavage, which provides the desulfonated aziridines and bixanthenyl X-X or bifluorenyl Fl-Fl, respectively. The SET path is favored by light. The competition is in favor of SET to the exclusion of the nucleophilic opening when trityl anion reacts with 1a. The twice-found byproducts 11 and 12 require the azirine intermediate 15, which is, at least formally, generated by elimination of TsH from 1a in a non-SET reaction.