Title | Synthesis of Diacetylene Macrocycles Derived from 1,2-Diethynyl Benzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer. |
Publication Type | Journal Article |
Year of Publication | 1994 |
Authors | Zhou, Q, Carroll, PJ, Swager, TM |
Journal | Journal of Organic Chemistry |
Volume | 59 |
Pagination | 1294–1301 |
ISSN | 0022-3263 |
Keywords | acetylene macrocyclic compd, alkynyl macrocyclic compd, diacetylene macrocyclic compd, solid state polymn diacetylene macrocycle |
Abstract | Diacetylene macrocycles I (R = H, C4H9, C6H13, C10H21, C12H25, OC10H21; n= 1-3) were prepd. from the oxidative coupling of 1,2-diethynylbenzene derivs. I can be produced in useful quantities and are of interest as precursors to novel conjugated org. polymers. The reported results indicate that when the R groups are large the dimeric macrocycle (n = 1) can be prepd. in as high as 74% yield from the corresponding 1,2-diethynylbenzene in a 1-step procedure. An alternate multistep procedure was found to produce the tetrameric macrocycle I (n = |
DOI | 10.1021/jo00085a016 |