Xenon difluoride (XeF,) reacts with alcohols t o form unstable alkoxyxenon fluoride intermediates (ROXeF). The regio-and stereo-chemistry of products from reaction of ROXeF with indene were determined. Alkoxyxenon fluorides [R = CH3, (CH,),CH, and (CH,),C] react as positive oxygen electrophiles (OE) when boron trifluoride-ether is used as catalyst. However, these alkoxyxenon fluorides react as apparent fluorine electrophiles (FE) with proton catalyst (hydrogen fluoride generated in situ). Reactions of XeF, and alcohols with electron-withdrawing substituents give alkoxyxenon fluorides which add to indene as an OE species even though boron trifluoride-ether was not used as catalyst. Reactions of XeF, with polynitroaliphatic alcohols and indene give rapid polymerization of indene rather than alkoxyfluorination.

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