Mass spectrometry in structural and stereochemical problems—CCXVI: Anomalous cleavage ions in bifunctional compounds resulting from participative interaction

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Abstract
Two types of remote group interaction after electron‐impact are possible: one involving the transfer of an atom or group of atoms and the other involving expulsion of a group of atoms concomitant with ring closure. These interactions were examined in a homologous series of polyfunctional compounds at high and low ionizing voltages. Fragmentation resulting from remote group interaction in hydroxy ethyleneketals occurs exclusively via 5‐, 6‐ and 7‐membered rings. This is contrasted with the remote group interaction of keto esters, diesters and other literature examples in which ring size (e.g. 5‐15‐membered) plays no significant role.

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