threo-C5H5(CO)2FeCHDCHDCH2SC6H5 | 122171-46-4

• 英文名称: threo-C5H5(CO)2FeCHDCHDCH2SC6H5
• CAS: 122171-46-4
• 化学式: C₁₆H₁₆FeO₂S
• 分子量: 330.199
• InChiKey: GZUKPZJEXSBCSQ-MGUJHANYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酸甲酯 、 threo-C5H5(CO)2FeCHDCHDCH2SC6H5 以 二氯甲烷 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  C5H5（CO）2Fe（CH2）3X电离形成环丙烷的立体化学及其机理

  摘要：

  Cyclopropane was produced efficiently both in the Ag+-assisted dissociation of bromide from C5H5(CO)2Fe(CH2)3Br (1) and in the dissociation of phenyl methyl sulfide from C5H5(CO)2Fe(CH2)3S(CH3)C6H5+CF3SO3- (8). Clean inversion of stereochemistry at the carbon bound to ion was seen in the formation of cis-1,2-dideuteriocyclopropane from the threo sulfonium salt C5H5(CO)2FeCHDCHDCH2S(CH3)C6H5+CF3SO3- (threo-8-d2). This stereochemical result is consistent with a W-shaped transition state for cyclopropane formation and rules out a mechanism involving a metallacyclobutane intermediate. A new explanation for the selective formation of cis cyclopropanes from the reaction of alkenes with (CO)5W = CHC6H5 is proposed in light of the results reported here.

  DOI：

  10.1021/om00038a036
• 作为产物：
  描述：

  sodium dicarbonyl(cyclopentadienyl)ferrate 、 以 四氢呋喃 为溶剂， 以82%的产率得到threo-C5H5(CO)2FeCHDCHDCH2SC6H5
  参考文献：
  名称：

  C5H5（CO）2Fe（CH2）3X电离形成环丙烷的立体化学及其机理

  摘要：

  Cyclopropane was produced efficiently both in the Ag+-assisted dissociation of bromide from C5H5(CO)2Fe(CH2)3Br (1) and in the dissociation of phenyl methyl sulfide from C5H5(CO)2Fe(CH2)3S(CH3)C6H5+CF3SO3- (8). Clean inversion of stereochemistry at the carbon bound to ion was seen in the formation of cis-1,2-dideuteriocyclopropane from the threo sulfonium salt C5H5(CO)2FeCHDCHDCH2S(CH3)C6H5+CF3SO3- (threo-8-d2). This stereochemical result is consistent with a W-shaped transition state for cyclopropane formation and rules out a mechanism involving a metallacyclobutane intermediate. A new explanation for the selective formation of cis cyclopropanes from the reaction of alkenes with (CO)5W = CHC6H5 is proposed in light of the results reported here.

  DOI：

  10.1021/om00038a036

文献信息

• Inversion of stereochemistry at the carbon bound to iron in cyclopropane formation from threo-C5H5(CO)2FeCHDCHDCH2S(CH3)C6H5+
  作者：Charles P. Casey、Laura J. Smith

  DOI：10.1021/om00111a038

  日期：1989.9