The Effect of Carbonyl Containing Substituents in the Terminal Chains on Mesomorphic Properties in Some Aromatic Esters and Thioesters 7. α-Keto Group on the Acid End of Phenylbenzoates and Thiobenzoates

M. E. Neubert Liquid Crystal Institute, Kent State University, Kent, OH, 44242; Chemistry Department, Kent State University, Kent, OH, 44242

R. B. Sharma Liquid Crystal Institute, Kent State University, Kent, OH, 44242; RBS, Day Chemical Laboratories, Inc., Fairborn, OH and MRJ, Chemistry Department, Harvard University, Cambridge, MA

C. Citano Liquid Crystal Institute, Kent State University, Kent, OH, 44242; Chemistry Department, Kent State University, Kent, OH, 44242

M. R. Jirousek Liquid Crystal Institute, Kent State University, Kent, OH, 44242; Chemistry Department, Kent State University, Kent, OH, 44242; RBS, Day Chemical Laboratories, Inc., Fairborn, OH and MRJ, Chemistry Department, Harvard University, Cambridge, MA

J. L. Paulin Liquid Crystal Institute, Kent State University, Kent, OH, 44242; Chemistry Department, Kent State University, Kent, OH, 44242

Abstract

withZ˭O Y˭C₁₀, OC₅, and Z˭S, Y˭C₅, C₁₀, OC₅ OC₁₂ were prepared by esterification of the α- keto acid with the appropriate phenol or thiol using the carbodiimide method. Mesomorphic properties were determined by hot-stage polarizing microscopy. The trend of a preference for a smectic A phase observed earlier in the analogous esters with Y˭C₉CO was also observed in these esters/thioesters. As expected, transition temperatures were higher than the analogous esters with a C₁₀, chain on the acid side.

The α-keto acid was synthesized by a Friedel-Crafts acylation of bromobenzene, protection of the α-keto group, conversion to the nitrile and hydrolysis of the nitrile and ketal groups. A new synthesis of a 4-alkoxybenzene thiol via sulfonation of an alkoxybenzene with CISO₃H followed by reduction is also reported.

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The Effect of Carbonyl Containing Substituents in the Terminal Chains on Mesomorphic Properties in Some Aromatic Esters and Thioesters 7. α-Keto Group on the Acid End of Phenylbenzoates and Thiobenzoates

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The Effect of Carbonyl Containing Substituents in the Terminal Chains on Mesomorphic Properties in Some Aromatic Esters and Thioesters 7. α-Keto Group on the Acid End of Phenylbenzoates and Thiobenzoates

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