CLAISEN REARRANGEMENT OF ALLYL ETHYL KETENE ACETALS GENERATED INSITU VIA BENZENESELENENIC ACID ELIMINATION

被引：33

作者：

PITTELOUD, R

PETRZILKA, M

机构：

[1] Départment de Chimie Organique, Universitè de Genève, Genève

来源：

HELVETICA CHIMICA ACTA | 1979年 / 62卷 / 04期

关键词：

D O I：

10.1002/hlca.19790620445

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Mixed acetals 7 of benzeneseleninylacetaldehyde, prepared by a simple 2‐step procedure from mono‐ and bicyclic allylic alcohols 5, undergo benzeneselenenic acid elimination to transient ketene acetals 8 which afford γ, δ‐unsaturated esters 9 via the ester Claisen rearrangement Scheme 2. Under the same conditions selenoxide 7h derived from benzyl alcohol 5h is converted back to benzyl alcohol with the concomitant formation of ethylphenylselenoacetate 12. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim

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页码：1319 / 1325

页数：7

相关论文

共 23 条

[1]

BENNETT GB, 1977, SYNTHESIS-STUTTGART, P589

[2] STUDIES ON COMPOUNDS RELATED TO AUXIN-A AND AUXIN-B .3. THE PREPARATION AND PROPERTIES OF THE CYCLOPENTENYL ANALOGUE OF AUXIN-B LACTONE [J].

BROWN, JB ;

HENBEST, HB ;

JONES, ERH .

JOURNAL OF THE CHEMICAL SOCIETY, 1950, (DEC) :3634-3641

[3] STEREOSPECIFIC ANGULAR ALKYLATION - NEW APPLICATION OF CLAISEN REARRANGEMENT [J].

BURGSTAHLER, A ;

NORDIN, IC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (01) :198-+

[4] STEREOSPECIFIC INTRODUCTION OF FUNCTIONALIZED ANGULAR METHYL GROUPS VIA CLAISEN REARRANGEMENT - OCTALIN AND HYDRINDENYL RING-SYSTEMS [J].

DAUBEN, WG ;

DIETSCHE, TJ .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (08) :1212-&

[5]

DAWSON DJ, 1968, TETRAHEDRON LETT, P1899

[6] REDUCTION OF SOME ENOLIZABLE BETA-DICARBONYL COMPOUNDS TO UNSATURATED ALCOHOLS BY LITHIUM ALUMINUM HYDRIDE .1. MONOCYCLIC BETA-KETOESTERS AND ALPHA-HYDROXYMETHYLENE KETONES [J].

DREIDING, AS ;

HARTMAN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (04) :939-943

[7] CLAISEN REARRANGEMENT OF ALLYL AND BENZYL ALCOHOLS WITH 1-DIMETHYLAMINO-1-METHOXYETHENE [J].

FELIX, D ;

GSCHWEND.K ;

WICK, AE ;

ESCHENMOSER, A .

HELVETICA CHIMICA ACTA, 1969, 52 (04) :1030-+

[8]

HEATHCOCK CH, 1971, TETRAHEDRON LETT, P4995

[9] SYNTHETIC APPLICATIONS OF ARYLSELENENIC AND ARYLSELENINIC ACIDS - CONVERSION OF OLEFINS TO ALLYLIC ALCOHOLS AND EPOXIDES [J].

HORI, T ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (09) :1689-1697

[10] SYNTHESIS OF DELTA8,9-AND DELTA9,10-OCTAL-1-ONE [J].

HOUSE, HO ;

THOMPSON, HW .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (10) :3729-&