Tricyclo[5.2.1.02,6]decadienone epoxides: rigid, highly congested α,β-epoxycyclopentanones with distinctive chemical behavior

J.H.M. Lange; N.A.J.M. Sommerdijk; P.P.M.A. Dols; E.G. Arnouts; A.J.H. Klunder; B. Zwanenburg

doi:10.1016/0040-4039(91)80707-D

Tricyclo[5.2.1.02,6]decadienone epoxides: rigid, highly congested α,β-epoxycyclopentanones with distinctive chemical behavior

J.H.M. Lange, N.A.J.M. Sommerdijk, P.P.M.A. Dols, E.G. Arnouts, A.J.H. Klunder, B. Zwanenburg

Onderzoeksoutput: Bijdrage aan tijdschrift › Tijdschriftartikel › Academic › peer review

8 Citaten (Scopus)

Samenvatting

Tricyclodecadienone epoxides 5 do not form an enolate on treatment with lithium diisopropyl amide. but instead undergo an unusual stereoselective β-hydride transfer leading to alcohols 6. The same type of epoxy endo-alcohol was obtained from parent epoxy ketone 5 on reaction with metal hydrides and organolithium reagents. These alcohols readily undergo an intramolecular epoxide migration by a Payne-type rearrangement, to give endo-epoxides 9.
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Originele taal-2	Engels
Pagina's (van-tot)	3127-3130
Tijdschrift	Tetrahedron Letters
Volume	32
Nummer van het tijdschrift	26
DOI's	https://doi.org/10.1016/0040-4039(91)80707-D
Status	Gepubliceerd - 24 jun 1991
Extern gepubliceerd	Ja

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10.1016/0040-4039(91)80707-D

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title = "Tricyclo[5.2.1.02,6]decadienone epoxides: rigid, highly congested α,β-epoxycyclopentanones with distinctive chemical behavior",

abstract = "Tricyclodecadienone epoxides 5 do not form an enolate on treatment with lithium diisopropyl amide. but instead undergo an unusual stereoselective β-hydride transfer leading to alcohols 6. The same type of epoxy endo-alcohol was obtained from parent epoxy ketone 5 on reaction with metal hydrides and organolithium reagents. These alcohols readily undergo an intramolecular epoxide migration by a Payne-type rearrangement, to give endo-epoxides 9..",

author = "J.H.M. Lange and N.A.J.M. Sommerdijk and P.P.M.A. Dols and E.G. Arnouts and A.J.H. Klunder and B. Zwanenburg",

year = "1991",

month = jun,

day = "24",

doi = "10.1016/0040-4039(91)80707-D",

language = "English",

volume = "32",

pages = "3127--3130",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "26",

}

Tricyclo[5.2.1.02,6]decadienone epoxides: rigid, highly congested α,β-epoxycyclopentanones with distinctive chemical behavior. / Lange, J.H.M.; Sommerdijk, N.A.J.M.; Dols, P.P.M.A.; Arnouts, E.G.; Klunder, A.J.H.; Zwanenburg, B.

In: Tetrahedron Letters, Vol. 32, Nr. 26, 24.06.1991, blz. 3127-3130.

Onderzoeksoutput: Bijdrage aan tijdschrift › Tijdschriftartikel › Academic › peer review

TY - JOUR

T1 - Tricyclo[5.2.1.02,6]decadienone epoxides: rigid, highly congested α,β-epoxycyclopentanones with distinctive chemical behavior

AU - Lange, J.H.M.

AU - Sommerdijk, N.A.J.M.

AU - Dols, P.P.M.A.

AU - Arnouts, E.G.

AU - Klunder, A.J.H.

AU - Zwanenburg, B.

PY - 1991/6/24

Y1 - 1991/6/24

N2 - Tricyclodecadienone epoxides 5 do not form an enolate on treatment with lithium diisopropyl amide. but instead undergo an unusual stereoselective β-hydride transfer leading to alcohols 6. The same type of epoxy endo-alcohol was obtained from parent epoxy ketone 5 on reaction with metal hydrides and organolithium reagents. These alcohols readily undergo an intramolecular epoxide migration by a Payne-type rearrangement, to give endo-epoxides 9..

AB - Tricyclodecadienone epoxides 5 do not form an enolate on treatment with lithium diisopropyl amide. but instead undergo an unusual stereoselective β-hydride transfer leading to alcohols 6. The same type of epoxy endo-alcohol was obtained from parent epoxy ketone 5 on reaction with metal hydrides and organolithium reagents. These alcohols readily undergo an intramolecular epoxide migration by a Payne-type rearrangement, to give endo-epoxides 9..

U2 - 10.1016/0040-4039(91)80707-D

DO - 10.1016/0040-4039(91)80707-D

M3 - Article

VL - 32

SP - 3127

EP - 3130

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 26

ER -