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

TitleSynthesis of Diacetylene Macrocycles Derived from 1,2-Diethynyl Benzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer.
Publication TypeJournal Article
Year of Publication1994
AuthorsZhou, Q, Carroll, PJ, Swager, TM
JournalJournal of Organic Chemistry
Volume59
Pagination1294–1301
ISSN0022-3263
Keywordsacetylene 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 =

DOI10.1021/jo00085a016