N-Deuterio-maleinsaeureimid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-Deuterio-maleinsaeureimid
• 英文别名: N-Deutero-maleinsaeureimid；N-Deuteriomaleinimid；Maleimid-d1；(1-~2~H)-1H-Pyrrole-2,5-dione；1-deuteriopyrrole-2,5-dione
• 化学式: C₄H₃NO₂
• 分子量: 98.0654
• InChiKey: PEEHTFAAVSWFBL-DYCDLGHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Deuterio-maleinsaeureimid 、 亚硝基叔丁烷 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Spin Adducts from the Reaction Between N-Phenyl-alpha-tert-butylnitrone (PBN) and Activated Olefins. A Facile Pathway Converting PBN into 2-Methyl-2-nitrosopropane (MNP).

  摘要：

  N-Phenyl-alpha-tert-butylnitrone (PBN) reacts with activated olefins RCH=CHR, such as maleimides, maleic anhydride or diethyl maleate, with formation of two types of persistent spin adducts giving characteristic EPR spectra, denoted types A and B. Spin adducts with type A spectrum were formed photochemically and identified as reductive coupling products between the olefin and PEN, RCH2CH(R)-PBN.. Spin adducts with type B spectra were formed photochemically and/or thermally and were identified as reductive coupling products RCH2CH(R)-N(O-.)Bu-t between the olefin and a degradation product of PEN, 2-methyl-2-nitrosopropane (MNP, t-BuNO).The conversion of PEN to t-BuNO was studied for a compound with an exceedingly reactive nitrogen-nitrogen double-bond, namely 4-phenyl-4H-1,2,4-triazoline-3,5-dione (PTAD). In this case, a 74% yield of t-BuNO was obtained in a short period of time; alpha,N-diphenylnitrone reacted similarly to give nitrosobenzene. The reaction between PEN and an activated olefin was assumed to occur analogously, either via the initial formation of a 1,3-dipolar cycloadduct or some parallel reaction involving attack of the electrophilic olefin at the PEN a-carbon. The 1,3-dipolar cycloadduct between PEN and N-phenylmaleimide exhibited favourable initiator properties for living polymerization of styrene.A new type of spin adduct, RCH(Bu-t)CH(R)-N(O-.)Bu-t, was prepared by the photochemical reaction between an activated olefin and t-BuNO. This reaction presumably proceeds by photocleavage of t-BuNO to NO and t-Bu-., the latter reacting with the activated olefin to give a transient radical, RCH(Bu-t)CH.(R), which is trapped by t-BuNO.

  DOI：

  10.3891/acta.chem.scand.52-1081

文献信息

• NAYAR M. S. B.; CALLERY P. S., J. ORG. CHEM., 1981, 46, NO 5, 1044-1045
  作者：NAYAR M. S. B.、 CALLERY P. S.

  DOI：——

  日期：——
• Spin Adducts from the Reaction Between N-Phenyl-alpha-tert-butylnitrone (PBN) and Activated Olefins. A Facile Pathway Converting PBN into 2-Methyl-2-nitrosopropane (MNP).
  作者：Lennart Eberson、Ola Persson、Kjartan Marøy、Alexander Krivokapic、Frode Rise、Anniken T. Øverås、Teófilo Rojo

  DOI：10.3891/acta.chem.scand.52-1081

  日期：——

  N-Phenyl-alpha-tert-butylnitrone (PBN) reacts with activated olefins RCH=CHR, such as maleimides, maleic anhydride or diethyl maleate, with formation of two types of persistent spin adducts giving characteristic EPR spectra, denoted types A and B. Spin adducts with type A spectrum were formed photochemically and identified as reductive coupling products between the olefin and PEN, RCH2CH(R)-PBN.. Spin adducts with type B spectra were formed photochemically and/or thermally and were identified as reductive coupling products RCH2CH(R)-N(O-.)Bu-t between the olefin and a degradation product of PEN, 2-methyl-2-nitrosopropane (MNP, t-BuNO).The conversion of PEN to t-BuNO was studied for a compound with an exceedingly reactive nitrogen-nitrogen double-bond, namely 4-phenyl-4H-1,2,4-triazoline-3,5-dione (PTAD). In this case, a 74% yield of t-BuNO was obtained in a short period of time; alpha,N-diphenylnitrone reacted similarly to give nitrosobenzene. The reaction between PEN and an activated olefin was assumed to occur analogously, either via the initial formation of a 1,3-dipolar cycloadduct or some parallel reaction involving attack of the electrophilic olefin at the PEN a-carbon. The 1,3-dipolar cycloadduct between PEN and N-phenylmaleimide exhibited favourable initiator properties for living polymerization of styrene.A new type of spin adduct, RCH(Bu-t)CH(R)-N(O-.)Bu-t, was prepared by the photochemical reaction between an activated olefin and t-BuNO. This reaction presumably proceeds by photocleavage of t-BuNO to NO and t-Bu-., the latter reacting with the activated olefin to give a transient radical, RCH(Bu-t)CH.(R), which is trapped by t-BuNO.