Preparation and Diels-Alder Reactions of 1,1-Dicarbonylalkenes

Thomas R Hoye; Andrew J. Caruso; Andrew S. Magee

doi:10.1021/jo00142a028

Preparation and Diels-Alder Reactions of 1,1-Dicarbonylalkenes

Thomas R Hoye, Andrew J. Caruso, Andrew S. Magee

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

1,1-Dicarbonyl- (ester, ketone, lactone) substituted alkenes are prepared from the corresponding saturated 1-phenylsulfinyl derivatives. These are formed from precursor sulfides, which can be efficiently prepared either by oxidation of β-hydroxy-α-phenylsulfenylcarbonyl compounds or direct acylation of α-phenylsulfenyl enolate anions with acid chlorides. Some of the title compounds can be isolated and then reacted while others are generated and reacted in situ in a Diels-Alder fashion with cyclopentadiene. Endo-exo selectivities are discussed.

Original language	English (US)
Pages (from-to)	4152-4156
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	47
Issue number	21
DOIs	https://doi.org/10.1021/jo00142a028
State	Published - 1982

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title = "Preparation and Diels-Alder Reactions of 1,1-Dicarbonylalkenes",

abstract = "1,1-Dicarbonyl- (ester, ketone, lactone) substituted alkenes are prepared from the corresponding saturated 1-phenylsulfinyl derivatives. These are formed from precursor sulfides, which can be efficiently prepared either by oxidation of β-hydroxy-α-phenylsulfenylcarbonyl compounds or direct acylation of α-phenylsulfenyl enolate anions with acid chlorides. Some of the title compounds can be isolated and then reacted while others are generated and reacted in situ in a Diels-Alder fashion with cyclopentadiene. Endo-exo selectivities are discussed.",

author = "Hoye, {Thomas R} and Caruso, {Andrew J.} and Magee, {Andrew S.}",

year = "1982",

doi = "10.1021/jo00142a028",

language = "English (US)",

volume = "47",

pages = "4152--4156",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Preparation and Diels-Alder Reactions of 1,1-Dicarbonylalkenes

AU - Hoye, Thomas R

AU - Caruso, Andrew J.

AU - Magee, Andrew S.

PY - 1982

Y1 - 1982

N2 - 1,1-Dicarbonyl- (ester, ketone, lactone) substituted alkenes are prepared from the corresponding saturated 1-phenylsulfinyl derivatives. These are formed from precursor sulfides, which can be efficiently prepared either by oxidation of β-hydroxy-α-phenylsulfenylcarbonyl compounds or direct acylation of α-phenylsulfenyl enolate anions with acid chlorides. Some of the title compounds can be isolated and then reacted while others are generated and reacted in situ in a Diels-Alder fashion with cyclopentadiene. Endo-exo selectivities are discussed.

AB - 1,1-Dicarbonyl- (ester, ketone, lactone) substituted alkenes are prepared from the corresponding saturated 1-phenylsulfinyl derivatives. These are formed from precursor sulfides, which can be efficiently prepared either by oxidation of β-hydroxy-α-phenylsulfenylcarbonyl compounds or direct acylation of α-phenylsulfenyl enolate anions with acid chlorides. Some of the title compounds can be isolated and then reacted while others are generated and reacted in situ in a Diels-Alder fashion with cyclopentadiene. Endo-exo selectivities are discussed.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

Preparation and Diels-Alder Reactions of 1,1-Dicarbonylalkenes

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