A synthesis of trifluoromethyl-substituted naphthalenes
A synthesis of trifluoromethyl-substituted naphthalenes
Alkyl and aryl Grignard reagents add to 1-(3,4-dihydro-2H-5-pyranyl)-2,2,2-trifluoro-1-ethanone by 1,4-addition, but benzyl Grignard reagents react in good yield by 1,2-addition. Dehydration of the resulting alcohols affords intermediate dienes, which readily undergo cyclisation to give substituted trifluoromethylnaphthalenes. Addition to other trifluoromethylketones permits access to a range of novel fluorinated naphthalenes and benzenes.
additions, grignard reagents, naphthalenes, trifluoromethylketones
grignard-reagents, carbonyl-compounds
7383-7386
Mellor, John M.
116e0a09-9f67-4a1e-8110-9a6f27772ed3
El-Sagheer, Afaf H.
0bf56d90-78ee-4772-add8-453ccacc39be
Salem Eedm, Ezz El-Din M.
b4f10321-b941-419a-9588-ed33c0430370
16 September 2000
Mellor, John M.
116e0a09-9f67-4a1e-8110-9a6f27772ed3
El-Sagheer, Afaf H.
0bf56d90-78ee-4772-add8-453ccacc39be
Salem Eedm, Ezz El-Din M.
b4f10321-b941-419a-9588-ed33c0430370
Mellor, John M., El-Sagheer, Afaf H. and Salem Eedm, Ezz El-Din M.
(2000)
A synthesis of trifluoromethyl-substituted naphthalenes.
Tetrahedron Letters, 41 (38), .
(doi:10.1016/S0040-4039(00)01254-5).
Abstract
Alkyl and aryl Grignard reagents add to 1-(3,4-dihydro-2H-5-pyranyl)-2,2,2-trifluoro-1-ethanone by 1,4-addition, but benzyl Grignard reagents react in good yield by 1,2-addition. Dehydration of the resulting alcohols affords intermediate dienes, which readily undergo cyclisation to give substituted trifluoromethylnaphthalenes. Addition to other trifluoromethylketones permits access to a range of novel fluorinated naphthalenes and benzenes.
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Published date: 16 September 2000
Keywords:
additions, grignard reagents, naphthalenes, trifluoromethylketones
grignard-reagents, carbonyl-compounds
Identifiers
Local EPrints ID: 18864
URI: http://eprints.soton.ac.uk/id/eprint/18864
ISSN: 0040-4039
PURE UUID: cf32c9ba-279d-4b13-897d-4d8713348a13
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Date deposited: 15 Dec 2005
Last modified: 15 Mar 2024 06:08
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Contributors
Author:
John M. Mellor
Author:
Afaf H. El-Sagheer
Author:
Ezz El-Din M. Salem Eedm
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