The Synthesis and Pyrolytic Rearrangement of Phthalate Esters of Some Tertiary Silanols. An Attempt to Prepare a Silicon Carbon Double Bond Species

1975 ◽  
Vol 53 (1) ◽  
pp. 67-70 ◽  
Author(s):  
K. G. Rutherford ◽  
R. J. Seidewand

The synthesis and pyrolysis of the methyl phthalate esters of diphenylmethylsilyl, t-butylsilyl, benzyldiphenylsilyl, and optically active 2-octanol yielded corresponding silyl ethers and phthalic anhydride. In the case of the latter compound, almost complete retention of configuration was observed about the asymmetric carbon atom. A mechanism is proposed for this rearrangement.

The experimental realization of the simplest possible types of molecular configuration which can show optical activity in the amorphous con­dition is important in connexion with stereochemical theory. Among optically active spiranes containing no asymmetric carbon atom such simple types are found in the d - and l -1-methyl- cyclo -hexylidene-4-acetic acids and the d - and 1-spiro- 5:5-dihydantoins, but no satisfactory case has hitherto been described of optical activity in substances of the constitution H —C—( CH 2 ) n —C—(CH 2 ) n —X X —C—( CH 2 ) n —C—(CH 2 ) n —H. One of the simplest conceivable examples of the latter kind should be found in the previously unknown symmetrical spiro -heptanediamine of the constitution— NH 2 —C—CH 2 —C—CH 2 —C—H H—C—CH 2 —C—CH 2 —C—NH 2 .


2012 ◽  
Vol 161 ◽  
pp. 128-133
Author(s):  
Li Wei Qian ◽  
Xiao Ling Hu ◽  
Ping Guan ◽  
Xiao Qing Guo

Novel Bi-Functional Magnetical Chiral Ionic Liquids (MCILs) Derived from Imidazolium and Pyridinium Were Synthesized via Simply Two Step Reactions. Optically Active Ionic Liquids Have an Asymmetric Carbon Atom Linked to the Positively Charged Imidazole Ring or Pyridine Ring, while the Magnetical Anion Contains Tetrachloroferrate (FeCl4-), their Properties of Chirality and Magnetism Were Characterized. the Structure of MCILs Would Promise a New Class of Bi-Functional Ionic Liquids.


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