BEHAVIOR OF ARYLAZO TERT-BUTYL SULFIDES WITH KETONE ENOLATES - COMPETITION BETWEEN SRN1 ALPHA-ARYLATION AND AZOCOUPLING REACTIONS
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DELLERBA, C
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
DELLERBA, C
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]
NOVI, M
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
NOVI, M
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]
PETRILLO, G
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
PETRILLO, G
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TAVANI, C
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
TAVANI, C
[1
]
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[1] CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
(Z)-Arylazo tert-butyl sulfides 1a-i react, in DMSO and at room temperature, with potassium acetone enolate to give good yields of 1-aryl-2-propanones via spontaneous S(RN)1 dark reactions. Alpha-Phenylation of pinacolone and acetophenone enolates by 1a likewise occurs in excellent yields. In agreement with the involvement of an electron-transfer catalyzed chain process, the reaction of the 4-bromo derivative 1n with pinacolone enolate gives mainly the bis-substitution product 13. With azosulfides 1j-m the arylation pathway competes with a base-induced thiol elimination eventually leading, depending on the structure of the azosulfide, to indazoles 8 or 11 and/or to 2-oxopropanal arylhydrazones 9, 10 or 12.
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
DELLERBA, C
NOVI, M
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
NOVI, M
PETRILLO, G
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
PETRILLO, G
TAVANI, C
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
TAVANI, C
BELLANDI, P
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
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IRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCEIRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCE
ESTEL, L
MARSAIS, F
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IRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCEIRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCE
MARSAIS, F
QUEGUINER, G
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IRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCEIRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCE
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
DELLERBA, C
NOVI, M
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
NOVI, M
PETRILLO, G
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
PETRILLO, G
TAVANI, C
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
TAVANI, C
BELLANDI, P
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CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALYCNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
机构:
IRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCEIRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCE
ESTEL, L
MARSAIS, F
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IRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCEIRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCE
MARSAIS, F
QUEGUINER, G
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IRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCEIRCOF,LCOFH,CHIM ORGAN FINE & HETEROCYCL LAB,INSA ROUEN BP 08,F-76131 MONT ST AIGNAN,FRANCE