Conjugate addition of grignard reagents to para-substituted nitrobenzenes
Nitrobenzenes bearing masked aldehyde, ketone and ketoester functions at the 4-position undergo conjugate addition with Grignard reagents in THF at − 15°C. Sequential treatment of the 4-substituted nitrobenzenes with primary or secondary alkyl magnesium halides followed by 2,3-dichloro-5,6-dicyano-1...
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| Published in | Journal of organometallic chemistry Vol. 447; no. 1; pp. 1 - 3 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Lausanne
Elsevier B.V
01.03.1993
Elsevier Science |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Nitrobenzenes bearing masked aldehyde, ketone and ketoester functions at the 4-position undergo conjugate addition with Grignard reagents in THF at − 15°C. Sequential treatment of the 4-substituted nitrobenzenes with primary or secondary alkyl magnesium halides followed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone affords the corresponding 2-alkylated derivatives in 50–80% yields. |
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| AbstractList | Nitrobenzenes bearing masked aldehyde, ketone and ketoester functions at the 4-position undergo conjugate addition with Grignard reagents in THF at − 15°C. Sequential treatment of the 4-substituted nitrobenzenes with primary or secondary alkyl magnesium halides followed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone affords the corresponding 2-alkylated derivatives in 50–80% yields. |
| Author | Bentley, Stephen J. Milner, David J. |
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| Cites_doi | 10.1055/s-1990-34093 10.1021/ar00099a005 10.1016/S0040-4039(00)98482-X |
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| Keywords | 1,2-Benzoquinone-2,3-dicarbonitrile(dichloro) Nitro compound Benzenic compound Grignard reaction THF |
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| References | Bartoli, Bosco, Dalpozzo (BIB1) 1985; 26 Polaczkowa, Jaworski, Wolinski (BIB2) 1953; 27 Bartoli (BIB4) 1984; 17 Makosza, Sienkiewicz, Wojciechowski (BIB3) 1990 Bartoli (10.1016/0022-328X(93)80265-D_BIB1) 1985; 26 Makosza (10.1016/0022-328X(93)80265-D_BIB3) 1990 Bartoli (10.1016/0022-328X(93)80265-D_BIB4) 1984; 17 Polaczkowa (10.1016/0022-328X(93)80265-D_BIB2) 1953; 27 |
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| SubjectTerms | Chemistry Exact sciences and technology Noncondensed benzenic compounds Organic chemistry Preparations and properties |
| Title | Conjugate addition of grignard reagents to para-substituted nitrobenzenes |
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