Grob Fragmentation - History

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

Albert Eschenmoser in 1952 investigated the base catalysed fragmentation of certain beta hydroxy ketones

Fragmentation reaction Eschenmoser 1952

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

Read more about this topic:  Grob Fragmentation

Famous quotes containing the word history:

    Anyone who is practically acquainted with scientific work is aware that those who refuse to go beyond fact rarely get as far as fact; and anyone who has studied the history of science knows that almost every great step therein has been made by the “anticipation of Nature.”
    Thomas Henry Huxley (1825–95)

    Don’t you realize that this is a new empire? Why, folks, there’s never been anything like this since creation. Creation, huh, that took six days, this was done in one. History made in an hour. Why it’s a miracle out of the Old Testament!
    Howard Estabrook (1884–1978)

    I think that Richard Nixon will go down in history as a true folk hero, who struck a vital blow to the whole diseased concept of the revered image and gave the American virtue of irreverence and skepticism back to the people.
    William Burroughs (b. 1914)