42046-61-7Relevant articles and documents
Preparation of O-Protected Cyanohydrins by Aerobic Oxidation of α-Substituted Malononitriles in the Presence of Diarylphosphine Oxides
Zhang, Dapeng,Lian, Mingming,Liu, Jia,Tang, Shukun,Liu, Guangzhi,Ma, Cunfei,Meng, Qingwei,Peng, Haisheng,Zhu, Daling
, p. 2597 - 2601 (2019/04/17)
A mild, reagent-cyanide-free, and efficient synthesis of O-phosphinoyl-protected cyanohydrins from readily available α-substituted malononitriles was realized using diarylphosphine oxides in the presence of O2. Mechanistic studies indicated that in addition to the initial aerobic oxidation of the malononitrile derivative notable features of this process include the formation of a tetrahedral intermediate and a subsequent intramolecular rearrangement. The phosphinoyl-protecting group can be removed by alcoholysis or by reduction with DIBAL-H.
Geminal Substituent Effects, 4. - The Dependence of the Inverse Anomeric Effect of Geminal Cyano Groups on the Structure
Beckhaus, Hans-Dieter,Dogan, Barbara,Pakusch, Joachim,Verevkin, Sergej,Ruechardt, Christoph
, p. 2153 - 2159 (2007/10/02)
The heats of combustion and the heats of sublimation of malodinitrile (1a), α-alkyl- (1b,c) and α,α-dialkylmalodinitriles (1d-f) have been determined.From the obtained standard heat of formation group increments for CH2, CH and C groups are deduced.The comparison of their values with the corresponding increments for monocyano alkanes reveals a synergetic destabilisation by two geminal cyano substituents of 11.5, 9.0, and 6.6 kcal/mol, respectively.Thus, this inverse anomeric effect decreases by increasing alkyl substitution.
