Abstrakti
The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.
Alkuperäiskieli | Englanti |
---|---|
Sivut | 1948-1958 |
Sivumäärä | 11 |
Julkaisu | Journal of Organic Chemistry |
Vuosikerta | 83 |
Numero | 4 |
DOI - pysyväislinkit | |
Tila | Julkaistu - 16 helmik. 2018 |
OKM-julkaisutyyppi | A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä |
Julkaisufoorumi-taso
- Jufo-taso 2
!!ASJC Scopus subject areas
- Organic Chemistry