Synthesis of Diacetylene Macrocycles Derived from 1, 2-Diethynyl Benzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer

Q Zhou, PJ Carroll, TM Swager

Index: Zhou, Qin; Carroll, Patrick J.; Swager, Timothy M. Journal of Organic Chemistry, 1994 , vol. 59, # 6 p. 1294 - 1301

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Citation Number: 205

Abstract

Diacetylene macrocycles 2-4 (n= 1-31 (R= H, C4H9, C6H13, C10H21, C12H25, OC10H21) have been prepared from the oxidative coupling of 1, 2-diethynylbenzene derivatives. These compounds can be produced in useful quantities and are of interest as precursors to novel conjugated organic polymers. The reported results indicate that when the R groups are large the dimeric macrocycle (n= 1) can be prepared in as high as 74% yield from the ...