Grob fragmentation

A Grob fragmentation is an elimination reaction that breaks a neutral aliphatic chain into three fragments: a positive ion spanning atoms 1 and 2 (the "electrofuge"), an unsaturated neutral fragment spanning positions 3 and 4, and a negative ion (the "nucleofuge") comprising the rest of the chain.

For example, the positive ion may be a carbenium, carbonium or acylium ion; the neutral fragment could be an alkene, alkyne, or imine; and the negative fragment could be a tosyl or hydroxyl ion:

The reaction is named for the Swiss chemist Cyril A. Grob.

Alternately, atom 1 could begin as an anion, in which case it becomes neutral rather than going from neutral to cationic.

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