Rearrangement of cis- and trans-2-Methyl-1-(substituted phenyl)isoindolinium 2-Methylides

Article abstract of DOI:10.1021/jo00080a024

Fluoride ion induced desilylation of cis-2-methyl-1-(substituted phenyl)-2-<(trimethylsilyl)methyl>isoindolinium iodides cis-5 gave mixtures of the Sommelet-Hauser rearrangement products 7 and the Stevens products 8 in a ratio about 8.5:1.5.Similar treatments of the trans-isomer (trans-5) afforded exclusively 8.The pathways of the ylide rearrangement are discussed.