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All 4 posts Subject: Carroll Rearrangement: Room Temp P2P Prep? Please login to post Down

Rhodium
(Chief Bee)
04-13-04 16:46
No 500591
User Picture       Carroll Rearrangement: Room Temp P2P Prep?

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)

Abstract
The Carroll rearrangement, a variant to the ester Claisen rearrangement, is a useful method for preparing ,-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
[sub]
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]

^{The Hive - Clandestine Chemists Without Borders}

hest
(Hive Adickt)
04-13-04 17:24
No 500601
      Litt.

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
(Newbee)
04-13-04 18:19
No 500609
User Picture       got it!

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...

W S F - for a better world.

Rhodium
(Chief Bee)
04-13-04 20:21
No 500642
User Picture       The Carroll rearrangement

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.rhodium.ws/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.

^{The Hive - Clandestine Chemists Without Borders}

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	All 4 posts		Subject: Carroll Rearrangement: Room Temp P2P Prep?		Please login to post		Down


		Rhodium (Chief Bee) 04-13-04 16:46 No 500591				Carroll Rearrangement: Room Temp P2P Prep?
						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) Abstract The Carroll rearrangement, a variant to the ester Claisen rearrangement, is a useful method for preparing ,-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 [sub] 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] ^{The Hive - Clandestine Chemists Without Borders}



		hest (Hive Adickt) 04-13-04 17:24 No 500601				Litt.
						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 (Newbee) 04-13-04 18:19 No 500609				got it!
						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... W S F - for a better world.



		Rhodium (Chief Bee) 04-13-04 20:21 No 500642				The Carroll rearrangement
						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.rhodium.ws/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. ^{The Hive - Clandestine Chemists Without Borders}

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