A joint experimental and ab initio study on the reactivity of several hydroxy selenides. Stereoselective synthesis of cis-disubstituted tetrahydrofurans via seleniranium ions

Michelangelo Gruttadauria; Carmela Aprile; Francesca D'Anna; Paolo Lo Meo; Serena Riela; Renato Noto

doi:10.1016/S0040-4020(01)00618-4

A joint experimental and ab initio study on the reactivity of several hydroxy selenides. Stereoselective synthesis of cis-disubstituted tetrahydrofurans via seleniranium ions

Michelangelo Gruttadauria, Carmela Aprile, Francesca D'Anna, Paolo Lo Meo, Serena Riela, Renato Noto

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

Abstract

The reactivity of several hydroxy selenides bearing an ethereal chain with catalytic amounts of perchloric acid in dichloromethane was investigated. Results showed that the position of the oxygen atom with respect to the seleniranium ring was crucial in order to get a good yield of the cyclized product. The factors on which yields of the 5-endo cyclization of the seleniranium ions depend were analysed by ab initio (HF/3-21G*) studies. An explanation of the different coordinating ability, towards the positively charged selenium atom, of the allylic OMe and homoallylic OH-2 groups was given.

Original language	English
Pages (from-to)	6815-6822
Number of pages	8
Journal	Tetrahedron
Volume	57
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4020(01)00618-4
Publication status	Published - 30 Jul 2001
Externally published	Yes

Keywords

Cyclizations
Oxygen heterocycles
Selenium
Theoretical studies

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10.1016/S0040-4020(01)00618-4

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title = "A joint experimental and ab initio study on the reactivity of several hydroxy selenides. Stereoselective synthesis of cis-disubstituted tetrahydrofurans via seleniranium ions",

abstract = "The reactivity of several hydroxy selenides bearing an ethereal chain with catalytic amounts of perchloric acid in dichloromethane was investigated. Results showed that the position of the oxygen atom with respect to the seleniranium ring was crucial in order to get a good yield of the cyclized product. The factors on which yields of the 5-endo cyclization of the seleniranium ions depend were analysed by ab initio (HF/3-21G*) studies. An explanation of the different coordinating ability, towards the positively charged selenium atom, of the allylic OMe and homoallylic OH-2 groups was given.",

keywords = "Cyclizations, Oxygen heterocycles, Selenium, Theoretical studies",

author = "Michelangelo Gruttadauria and Carmela Aprile and Francesca D'Anna and {Lo Meo}, Paolo and Serena Riela and Renato Noto",

year = "2001",

month = jul,

day = "30",

doi = "10.1016/S0040-4020(01)00618-4",

language = "English",

volume = "57",

pages = "6815--6822",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "31",

}

A joint experimental and ab initio study on the reactivity of several hydroxy selenides. Stereoselective synthesis of cis-disubstituted tetrahydrofurans via seleniranium ions. / Gruttadauria, Michelangelo; Aprile, Carmela; D'Anna, Francesca et al.
In: Tetrahedron, Vol. 57, No. 31, 30.07.2001, p. 6815-6822.

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

TY - JOUR

T1 - A joint experimental and ab initio study on the reactivity of several hydroxy selenides. Stereoselective synthesis of cis-disubstituted tetrahydrofurans via seleniranium ions

AU - Gruttadauria, Michelangelo

AU - Aprile, Carmela

AU - D'Anna, Francesca

AU - Lo Meo, Paolo

AU - Riela, Serena

AU - Noto, Renato

PY - 2001/7/30

Y1 - 2001/7/30

N2 - The reactivity of several hydroxy selenides bearing an ethereal chain with catalytic amounts of perchloric acid in dichloromethane was investigated. Results showed that the position of the oxygen atom with respect to the seleniranium ring was crucial in order to get a good yield of the cyclized product. The factors on which yields of the 5-endo cyclization of the seleniranium ions depend were analysed by ab initio (HF/3-21G*) studies. An explanation of the different coordinating ability, towards the positively charged selenium atom, of the allylic OMe and homoallylic OH-2 groups was given.

AB - The reactivity of several hydroxy selenides bearing an ethereal chain with catalytic amounts of perchloric acid in dichloromethane was investigated. Results showed that the position of the oxygen atom with respect to the seleniranium ring was crucial in order to get a good yield of the cyclized product. The factors on which yields of the 5-endo cyclization of the seleniranium ions depend were analysed by ab initio (HF/3-21G*) studies. An explanation of the different coordinating ability, towards the positively charged selenium atom, of the allylic OMe and homoallylic OH-2 groups was given.

KW - Cyclizations

KW - Oxygen heterocycles

KW - Selenium

KW - Theoretical studies

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U2 - 10.1016/S0040-4020(01)00618-4

DO - 10.1016/S0040-4020(01)00618-4

M3 - Article

AN - SCOPUS:0035974349

SN - 0040-4020

VL - 57

SP - 6815

EP - 6822

JO - Tetrahedron

JF - Tetrahedron

IS - 31

ER -

A joint experimental and ab initio study on the reactivity of several hydroxy selenides. Stereoselective synthesis of cis-disubstituted tetrahydrofurans via seleniranium ions

Abstract

Keywords

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