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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