ArticleBeilstein journal of organic chemistry2016
Solving the puzzling competition of the thermal C(2)-C(6) vs Myers-Saito cyclization of enyne-carbodiimides.
Article in Beilstein journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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1 citing paper in PubMed.
- Development of an Allenyne-Alkyne [4+2] Cycloaddition and its Application to Total Synthesis of Selaginpulvilin A.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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4 authors.
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Abstract
The mechanism of the thermal cyclization of enyne-carbodiimides 7a-c has been studied computationally by applying the DFT method. The results indicate that enyne-carbodiimides preferentially follow the C(2)-C(6) (Schmittel) cyclization pathway in a concerted fashion although the Myers-Saito diradical formation is kinetically preferred. The experimentally verified preference of the C(2)-C(6) over the Myers-Saito pathway is guided by the inability of the Myers-Saito diradical to kinetically compete in the rate-determining trapping reactions, either inter- or intramolecular, with the concerted C(2)-C(6) cyclization. As demonstrated with enyne-carbodiimide 11, the Myers-Saito channel can be made the preferred pathway if the trapping reaction by hydrogen transfer is no more rate determining.
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