Synthesis, Structure, and Reactivity of Enediyne Macrocycles
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (13) , 4258-4261
- https://doi.org/10.1021/jo9600971
Abstract
The reaction of bis-propargyl bromide enediyne 4 with weakly basic nucleophiles allows the facile synthesis of acyclic and macrocyclic enediynes. Depending on the bis-nucleophile employed, 12- to 16-membered enediyne macrocycles were obtained. The thermal stability of the new cyclic enediynes was investigated by differential scanning calorimetry. Upon coordination of the macrocycle 5c with Hg(O2CCF3)2, a drop of the enediyne cyclization temperature of nearly 100 K was observed.Keywords
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