Ortho effects in organic molecules on electron impact. Part 15. Oxygen transfers from the nitro group to both sulphur and olefinic double bonds in allyl o†nitrophenyl sulphide

An oxygen transfer from the nitro group to the CC group, followed by a simple cleavage, afford intense fragments corresponding to o‐nitrosothiophenol at m/z 139 and o‐nitrosothiophenoxy cation at m/z 138 during mass spectral fragmentations of allyl o‐nitrophenyl sulphide. Further, a concerted double oxygen transfer from the nitro group to the sulphur is proposed for the ejection of ṠO2H from the molecular ion of this compound, leading to the quinolinium cation at m/z 130. These processes are supported by the high‐resolution data, collision‐induced dissociation linked‐scan spectra and chemical evidence. Copyright © 1989 John Wiley & Sons, Ltd.