Studies on structurally simple αβ-butenolides. IV. behaviour of protoanemonin as electrophile towards alcohols and thiols

A. Calderon; J. Font; R. M. Ortuno

doi:10.1016/S0040-4020(01)88808-6

Studies on structurally simple αβ-butenolides. IV. behaviour of protoanemonin as electrophile towards alcohols and thiols

A. Calderon, J. Font, R. M. Ortuno

Departament de Química

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Protoanemonin, reacts in different ways with thiolate and alkoxide anions. Thus, while the very soft nucleophile benzenethiolate attacks exclusively the olefinic carbons of 1, alkoxides always attack the carbonyl group in the first step of the reaction. In intermediate cases, when neither very hard nor very soft nucleophiles are used, regioselectivity is not observed. Mechanisms are discussed to explain this differential reactivity. © 1984.

Idioma original	Anglès
Pàgines (de-a)	3787-3794
Revista	Tetrahedron
Volum	40
Número	19
DOIs	https://doi.org/10.1016/S0040-4020(01)88808-6
Estat de la publicació	Publicada - 1 de gen. 1984

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10.1016/S0040-4020(01)88808-6

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title = "Studies on structurally simple αβ-butenolides. IV. behaviour of protoanemonin as electrophile towards alcohols and thiols",

abstract = "Protoanemonin, reacts in different ways with thiolate and alkoxide anions. Thus, while the very soft nucleophile benzenethiolate attacks exclusively the olefinic carbons of 1, alkoxides always attack the carbonyl group in the first step of the reaction. In intermediate cases, when neither very hard nor very soft nucleophiles are used, regioselectivity is not observed. Mechanisms are discussed to explain this differential reactivity. {\textcopyright} 1984.",

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AU - Calderon, A.

AU - Font, J.

AU - Ortuno, R. M.

PY - 1984/1/1

Y1 - 1984/1/1

N2 - Protoanemonin, reacts in different ways with thiolate and alkoxide anions. Thus, while the very soft nucleophile benzenethiolate attacks exclusively the olefinic carbons of 1, alkoxides always attack the carbonyl group in the first step of the reaction. In intermediate cases, when neither very hard nor very soft nucleophiles are used, regioselectivity is not observed. Mechanisms are discussed to explain this differential reactivity. © 1984.

AB - Protoanemonin, reacts in different ways with thiolate and alkoxide anions. Thus, while the very soft nucleophile benzenethiolate attacks exclusively the olefinic carbons of 1, alkoxides always attack the carbonyl group in the first step of the reaction. In intermediate cases, when neither very hard nor very soft nucleophiles are used, regioselectivity is not observed. Mechanisms are discussed to explain this differential reactivity. © 1984.

U2 - 10.1016/S0040-4020(01)88808-6

DO - 10.1016/S0040-4020(01)88808-6

M3 - Article

SN - 0040-4020

VL - 40

SP - 3787

EP - 3794

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

Studies on structurally simple αβ-butenolides. IV. behaviour of protoanemonin as electrophile towards alcohols and thiols

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