Abstrakti
This work describes the first formal cycloaddition reaction of photogenerated nucleophilic carbenes derived from acylsilanes with electrophilic dienes. The resulting transient donor-Acceptor cyclopropane rearranges to its stable and highly functionalized cyclopentene isomer in an unprecedented metal-free process. The cyclopropanation-vinyl cyclopropane rearrangement sequence was corroborated by computational calculations. The cyclopropane formation corresponds to a higher energetic barrier, and the vinylcyclopropane-cyclopentene rearrangement proceeds through different mechanisms, although of comparable energies, depending on the stereochemistry of the cyclopropane.
Alkuperäiskieli | Englanti |
---|---|
Sivut | 8910-8920 |
Sivumäärä | 11 |
Julkaisu | Journal of Organic Chemistry |
Vuosikerta | 87 |
Numero | 14 |
DOI - pysyväislinkit | |
Tila | Julkaistu - 23 heinäk. 2022 |
OKM-julkaisutyyppi | A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä |
Julkaisufoorumi-taso
- Jufo-taso 2
!!ASJC Scopus subject areas
- Organic Chemistry