Protonation of P-Stereogenic Phosphiranes: Phospholane Formation via Ring Opening and C-H Activation.

ABSTRACT: Protonation of cyclopropanes and aziridines is well-studied, but reactions of phosphiranes with acids are rare and have not been reported to result in ring opening. Treatment of syn-Mes*PCH₂CHR (Mes* = 2,4,6-(t-Bu)₃C₆H₂, R = Me or Ph, syn-1-2) or anti-Mes*PCH₂CHPh (anti-2) with triflic acid resulted in regiospecific anti-Markovnikov C-protonation with ring opening and cyclophosphination of a Mes* ortho-t-Bu group to yield the phospholanium cations [PH(CH₂CH₂R)(4,6-(t-Bu)₂-2-CMe₂CH₂C₆H₂)][OTf] (R = Me or Ph, 3-4), which were deprotonated with NEt₃ to giv

SUBMITTER: Tipker RM 

PROVIDER: S-EPMC10077540 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature