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Wharton-Grob fragmentation

The Wharton-Grob fragmentation and the cationic cyclisation of polyolefins. Synthesis o/Cecropia juvenile hormone and d, -progesterone. [Pg.376]

The less hindered peripheric secondary hydroxyl group of the key intermediate 28 was chemoselectively tosylated (29), submitted to an internal Wharton-Grob fragmentation (30). After attack on the carbonyl group (3i) with methyllithium and activation of the secondary alcohol as the corresponding tosylate, the resulting... [Pg.378]

This reaction is related to the Bamford-Stevens Reaction, Grob Fragmentation and Wharton Rearrangement. [Pg.1006]

Table 13. Cycloheptenones by Grob- Wharton Fragmentation of Bicyclo[3.2.0]heptan-l-ol Derivatives... Table 13. Cycloheptenones by Grob- Wharton Fragmentation of Bicyclo[3.2.0]heptan-l-ol Derivatives...
A base-catalyzed Grob-Wharton fragmentation of a hydroxybicyclo[5.4.0]nonyl sulfone 3 yielded a cyclononenone derivative 4.193 The reaction is initiated by lactone cleavage with powdered potassium hydroxide in methanol, whereas sodium methoxide was not successful. [Pg.600]

Methoxide promoted lactone cleavage in a tricyclic sulfone initiated a Grob-Wharton fragmentation which gave a cycloundecadienone derivative 1 in refluxing methanol.210... [Pg.603]

This reaction type is called a Grob as well as a Wharton fragmentation [1] [2]. [Pg.164]


See other pages where Wharton-Grob fragmentation is mentioned: [Pg.374]    [Pg.376]    [Pg.379]    [Pg.561]    [Pg.288]    [Pg.374]    [Pg.376]    [Pg.379]    [Pg.561]    [Pg.288]    [Pg.331]    [Pg.371]    [Pg.563]    [Pg.1055]    [Pg.526]    [Pg.253]    [Pg.453]    [Pg.1055]    [Pg.185]    [Pg.563]    [Pg.573]    [Pg.587]    [Pg.587]    [Pg.480]    [Pg.368]    [Pg.308]    [Pg.254]   


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Grob fragmentation

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