phenoxymethylfluorocarbene | 137720-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: phenoxymethylfluorocarbene
• CAS: 137720-23-1
• 化学式: C₈H₇FO
• 分子量: 138.141
• InChiKey: AGXJHYQIQILCQW-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  phenoxymethylfluorocarbene 生成 (Z)-1-fluoro-2-phenoxyethene
  参考文献：
  名称：

  Kinetics of alkylhalocarbene rearrangements: modulation by fluorine substituents

  摘要：

  Rate constants were measured by laser flash photolytic methods for hydrogen and carbon 1,2-migrations in four different alkylchlorocarbenes and in the analogous alkylfluorocarbenes. The carbenes, products, and rate constants (s-1) were as follows: phenoxymethylchlorocarbene to (Z)- and (E)-1-chloro-2-phenoxyethene (Z/E approximately 4/1), k = 3.6 x 10(7); phenoxymethylfluorocarbene to (Z)-1-fluoro-2-phenoxyethene (Z/E > 10/1), k = 1.3 x 10(7); neopentylchlorocarbene to (Z)- and (E)-1-tert-butyl-2-chloroethene (Z/E = 1/12), k = 1.4 x 10(7); neopentylfluorocarbene to (Z)- and (E)-1-tert-butyl-2-fluoroethene (Z/E = 1/2.5), k = 2.6 X 10(6); cyclobutylchlorocarbene to 1-chlorocyclopentene (C migration) and chloromethylenecyclobutane (H migration), k(c) = 4.6 X 10(7), k(H) = 2.1 X 10(7); cyclobutylfluorocarbene to 1-fluorocyclopentene (C migration) and fluoromethylenecyclobutane (H migration), k(c) = 1.8 x 10(6), k(H) = 5.3 x 10(5); cyclopropylchlorocarbene to 1-chlorocyclobutene, k = 9 x 10(5); cyclopropylfluorocarbene to 1-fluorocyclobutene, k = 1.4 x 10(5). Activation energies for several of these processes were in the range of 2-4 kcal/mol, with A approximately 10(8)-10(9) s-1.

  DOI：

  10.1021/ja00029a025

文献信息

• The kinetic range of carbene–pyridine ylide forming reactions
  作者：Chuan-Sheng Ge、Eun G. Jang、Elizabeth A. Jefferson、Weiguo Liu、Robert A. Moss、Joanna Włostowska、Song Xue

  DOI：10.1039/c39940001479

  日期：——

  Absolute rate constants for the ylide-forming reactions of 16 carbenes with pyridine range from 1.4 × 1010 to 1.2 × 105 dm3 mol–1 s–1, and can be rationalized by frontier molecular orbital theory.

  16种卡宾与吡啶反应形成的烯醇基反应的绝对速率常数范围从1.4 × 10¹⁰到1.2 × 10⁵ dm³ mol⁻¹ s⁻¹，可以通过前沿分子轨道理论进行合理解释。