- Halogenated analogs of tri-O-thymotide (TOT) and Tri-3-(2-butyl)-6-methylsalicylide (TSBS): Synthesis and clathration studies
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Halogenated trisalicylide derivatives 1-6, representing three-fold symmetric C3 'homo trimers' as well as dissymmetric C1 'mixed trimers' have been synthesized. Clathration studies indicate that these halogenated TOT analogs do not f
- Gnaim,Keehn,Green
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p. 2883 - 2886
(2007/10/02)
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- Improved Preparation of the Clathrate Host Compound Tri-o-thymotide and Related Trisalicylide Derivatives
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In order to improve the relatively low yield (ca. 35percent) previously observed in the synthesis of tri-o-thymotide (TOT, 1) from o-thymotic acid (2), the cyclodehydration was studied using a variety of conditions.The low yield is due to the formation of di-o-thymotide (DOT, 3), previously reported, and at least three other products (4-6), which apparently result from the acid-catalyzed decarboxylation of 2 and subsequent condensation with thymol (7).Using pyridine as a solvent, side-product formation is inhibited.Under appropriate conditions, namely, neat POCl3 at 50 deg C, the yield of 1 is 93percent.Other salicylic acid derivatives also give high yields of the corresponding "trimers" under these conditions, thus providing a general, improved preparation of a family of potential clathrate host substances.
- Gnaim, Jallal M.,Green, Bernard S.,Arad-Yellin, Rina,Keehn, Philip M.
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p. 4525 - 4529
(2007/10/02)
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