Sonochemical synthesis of norbornane derivatives using allene cyclopentadiene Diels-Alder cycloaddition

C. Paul Raj; N. Arul Dhas; M. Cherkinski; A. Gedanken; S. Braverman

doi:10.1016/S0040-4039(98)01016-8

Sonochemical synthesis of norbornane derivatives using allene cyclopentadiene Diels-Alder cycloaddition

C. Paul Raj, N. Arul Dhas, M. Cherkinski, A. Gedanken, S. Braverman

Department of Chemistry

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18 Scopus citations

Abstract

The dienophilic reactivity of allenic trichloromethyl sulfoxides under ultrasound irradiation has been investigated. A considerable rate enhancement has been observed for cycloaddition of the and γ-monosubstituted allenyl trichloromethyl sulfoxides to cyclopentadiene. With the corresponding γ,γ- disubstituted allenic sulfoxides, a competing 1,2- to 1,3-diene isomerization is observed.

Original language	English
Pages (from-to)	5413-5416
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4039(98)01016-8
State	Published - 23 Jul 1998

Bibliographical note

Funding Information:
spectra. One of us (CPR) acknowledges the financial assistance from the Bar-Ilan University.

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title = "Sonochemical synthesis of norbornane derivatives using allene cyclopentadiene Diels-Alder cycloaddition",

abstract = "The dienophilic reactivity of allenic trichloromethyl sulfoxides under ultrasound irradiation has been investigated. A considerable rate enhancement has been observed for cycloaddition of the and γ-monosubstituted allenyl trichloromethyl sulfoxides to cyclopentadiene. With the corresponding γ,γ- disubstituted allenic sulfoxides, a competing 1,2- to 1,3-diene isomerization is observed.",

author = "Raj, {C. Paul} and Dhas, {N. Arul} and M. Cherkinski and A. Gedanken and S. Braverman",

note = "Funding Information: spectra. One of us (CPR) acknowledges the financial assistance from the Bar-Ilan University.",

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doi = "10.1016/S0040-4039(98)01016-8",

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AU - Raj, C. Paul

AU - Dhas, N. Arul

AU - Cherkinski, M.

AU - Gedanken, A.

AU - Braverman, S.

N1 - Funding Information: spectra. One of us (CPR) acknowledges the financial assistance from the Bar-Ilan University.

PY - 1998/7/23

Y1 - 1998/7/23

N2 - The dienophilic reactivity of allenic trichloromethyl sulfoxides under ultrasound irradiation has been investigated. A considerable rate enhancement has been observed for cycloaddition of the and γ-monosubstituted allenyl trichloromethyl sulfoxides to cyclopentadiene. With the corresponding γ,γ- disubstituted allenic sulfoxides, a competing 1,2- to 1,3-diene isomerization is observed.

AB - The dienophilic reactivity of allenic trichloromethyl sulfoxides under ultrasound irradiation has been investigated. A considerable rate enhancement has been observed for cycloaddition of the and γ-monosubstituted allenyl trichloromethyl sulfoxides to cyclopentadiene. With the corresponding γ,γ- disubstituted allenic sulfoxides, a competing 1,2- to 1,3-diene isomerization is observed.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Sonochemical synthesis of norbornane derivatives using allene cyclopentadiene Diels-Alder cycloaddition

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