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An unusual effect of the nitro substituent in the Type II photoelimination reactions of aryl ketones

✍ Scribed by Richard R. Hautala; Thomas Mayer

Book ID
104236056
Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
237 KB
Volume
18
Category
Article
ISSN
0040-4039

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✦ Synopsis

The influence of ring substituents on aromatic catbonyl photochemistry has received considerable attention .' The most thoroughly studied photopmcess in this regard is hydrogen abstraction.

An intramolecular example is illustrated below.

It is well known that electron-donating substituents &crease the rote constant A r -h

for the initial abstraction and that electron-withdrawing substituents enhance this ~rocess.~ However, unless the rate constant for hydrogen abstraction is quite low (<107sec-'), other processes available to deacti-

πŸ“œ SIMILAR VOLUMES

The reaction of o-amino aryl carboxylic
The reaction of o-amino aryl carboxylic acids with Grignard reagents. The unusual effect of the N-protecting group on aryl ketone formation
✍ Puwen Zhang; Eugene A Terefenko; Joseph Slavin πŸ“‚ Article πŸ“… 2001 πŸ› Elsevier Science 🌐 French βš– 54 KB

The addition of Grignard reagents to the o-amino aryl carboxylic acids without any additive forms the tertiary carbinol as a major product. Unexpectedly, the aryl ketones are formed as the only isolated product if o-amino moiety of anthranilic acids is protected with Boc, trifluoroacetyl, and pivalo