Glycidol dimers

N. Borho and M. A. Suhm, Glycidol dimer Anatomy of a molecular handshake. Phys. Chem. Chem. Phys. 4, 2721 2732 (2002). 

Shum et al. [106] carried out supersonic jet FTIR experiments on the chiral discrimination of neutral glycidol dimers (Fig. 3.8). 

N. Borho et al., Chiral self-recognition in the gas phase The case of glycidol dimers. Phys. Chem. Chem. Phys. 3, 1945-1948 (2001)... 

Figure 6.6 shows our synthetic plan for testudinariol A (149). Because the structural feature of target molecule 149 is its C2-symmetry, 149 can be obtained by dimerization or its equivalent operation of A. The intermediate A may be prepared from B by (Z)-selective installation of the two-carbon appendage. For the stereoselective construction of the cyclopentane portion of B, an intramolecular ene reaction is appropriate employing C as the substrate. The intramolecular oxy-Michael-type cyclization of D has been adopted to prepare the tetrahydropyran ring of C. The intermediate D can be synthesized from F [(R)-glycidol] via the known diol E. 

At 26.7 mbar pressure 40% weight toss main product is 2,4-diphenyl thiophene at least 11 unidentified minor products CO2, H2O, butene, isobutene, dimethyl ketene, styrene, methacrylic acid, succinic-type 5-membered cyclic anhydrides Chlorotrifluoroethylene, styrene, HQ, chloropentafluoropropene, ethene, chloroethene, totuene, a-melhylstyiene, dimer and trimer structures with some unsaturation S1F4 (fiom reaction of HF with glass). Distribution of products varies with polymer composition CO, CO2, propene, isobutene, dimethyl ketene, acrolein, allyl alcohol, toluene, styrene, cl-methylstyrene, ethylbenzene, glycidol, glycidylmethacrylate product distribution depends on copolymer composition... 

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