New P-alkyl 7-phospanorbornenes; Synthesis, oxidation, fragmentation-related phosphorylation, and deoxygenation

GRAPHICAL ABSTRACT

ABSTRACT

A series of 1-alkyl-3-methyl-2,5-dihydro-1H-phosphole oxides were converted to the corresponding 7-phosphanorbornene 7-oxides by Diels–Alder reaction. New P-alkyl 2,3 oxaphosphabicyclo[2.2.2]octene 3-oxides were synthesized by the Bayer–Villiger oxidation of the 7-phosphanorbornene 7-oxides that were used as precursors for reactive alkylmetaphosphonates useful in the phosphonylation of alcohols. Finally, the P-alkyl phosphole-oxide dimers were converted to phosphine–boranes with dimethyl sulfide–borane.

KEYWORDS:

• 1H-phosphole oxides
• 7-phosphanorbornene 7-oxides
• Diels–Alder cycloaddition
• fragmentation
• microwave
• phosphonylation

Funding

This project was supported by the Hungarian Research Development and Innovation Fund (K119202). T. Kovács is grateful for the fellowship provided by Chinoin-Sanofi.