Cleavage of ethers and geminal diacetates using the boron triiodide-N,N-diethylaniline complex

Article abstract of DOI:10.1016/S0040-4039(00)97220-4

The boron triiodide-N,N-diethylaniline complex, generated in situ from borane:N,N-diethylaniline and iodine cleaves ethers and regenerates carbox-aldehydes from the corresponding geminal diacetate derivatives under mild conditions in good yields. Recently a simple procedure for the preparation of alkyl and alkenyl iodides in good yields using boron triiodide-N,N-diethylaniline complex and acetic acid was reported.¹ This prompted us to report our results on the cleavage of ethers and regeneration of aldehydes from geminal diacetates using the boron triiodide-N,N-diethylaniline reagent.