History
An early instance of fragmentation is the dehydration of di(tert-butyl)methanol yielding 2-methyl-2-butene and isobutene, a reaction described in 1933 by Frank C. Whitmore. This reaction proceeds by formation of a secondary carbocation followed by a rearrangement reaction to a more stable teriary carbocation and elimination of a t-butyl cation.
| Fragmentation reaction Whitmore 1933 |
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Albert Eschenmoser in 1952 investigated the base catalysed fragmentation of certain beta hydroxy ketones
| Fragmentation reaction Eschenmoser 1952 |
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The original work published by Grob (1955) concerns the formation of 1,5-hexadiene from cis or trans 1,4-dibromocyclohexane by sodium metal. According to reviewers Prantz and Mulzer in 2010 the name Grob fragmentation was chosen in more or less glaring disregard of the earlier contributions.
| Grob fragmentation 1955 |
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Read more about this topic: Grob Fragmentation
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