Carroll Rearrangement: Room Temp P2P Prep?

[Rhodium]

This is really frustrating... I have no idea how to aquire any more info on this exciting ACS conference abstract...

The Carroll Rearrangement: A Facile Entry Into Phenylacetone and Related Derivatives
Kirk L. Sorgi and Lorraine Scott
^{Department of Chemical Development, R. W. Johnson Pharmaceutical Research Institute, Spring House, PA. 19477}
Abstracts of Papers of the American Chemical Society 200(2), 297-ORGN (1990)


https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000500591-carroll.gif" target="_blank" title="View this image">

Abstract
The Carroll rearrangement, a variant to the ester Claisen rearrangement, is a useful method for preparing https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000500591-file_lwwo.gif" title="View this image">,https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000500591-file_feqa.gif" title="View this image">-unsaturated ketones from allylic acetoacetates. The reaction has found limited action in synthetic organic chemistry due to the harsh thermal conditions normally needed to induce the [3,3]-sigmatropic rearrangement. While examining the chemistry involving allylic acetoacetate I, we encountered a mild (room temperature) Carroll rearrangement that afforded the phenylacetone derivative III via keto-acid II. Several examples showing the generality, scope, and limitations of the methodology will be described along with mechanistic considerations.


Carroll Rearrangement References

http://themerckindex.cambridgesoft.com/TheMerckIndex/NameReactions/ONR69.htm

http://www.chempensoftware.com/reactions/RXN045.htm

http://www.chem.ox.ac.uk/thirdyearcomputing/reactioninfo.asp?id=207%5B/sub

]

[hest]

Beilstein turned up with thois one.
Wessely; MOCMB7; Monatsh.Chem.; 90; 1959; 713, 718.
Iff you have it online (i don't) it might be worth a look

[kurupira]

ref. is Tetrahedron Letters, Vol. 36, No. 21, pp. 3597-3600, 1995.

"The Carroll Rearrangement:
A Facile Entry into Substituted Arylacetones
and Related Derivatives

Kirk L. Sorgi,* Lorraine Scott, and Cynthia A. Maryanoff
Chemical Development Department
The R. W. Johnson Pharmaceutical Research Institute
Spring House, PA 19477 USA

Abstract: Acetoacetates, easily prepared from substituted p-quinols, undergo a mild room temperature
Carroll rearrangement to afford substituted arylacetones and related derivatives in moderate to good
yields...."

Rhodium
If you want the pdf ask me by pm...

[Rhodium]

Thanks Kurupira! Here's the full article - It was way stranger chemistry than I imagined...

The Carroll rearrangement: A facile entry into substituted arylacetones and related derivatives
Kirk L. Sorgi, Lorraine Scott and Cynthia A. Maryanoff

Tetrahedron Letters 36(21), 3597-3600 (1995)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/carroll.rearrangement.pdf)

Abstract
Acetoacetates, easily prepared from substituted p-quinols, undergo a mild room temperature Carroll rearrangement to afford substituted arylacetones and related derivatives in moderate to good yields.