Preparation of the Maleic Anhydride Nucleus from Dichloro gamma-Lactams: Focus on the Role of the N-Substituent in the Functional Rearrangement and in the Hydrolytic Steps

Franco Ghelfi; Mariella Pattarozzi; Fabrizio Roncaglia; Andrew F. Parsons; Fulvia Felluga; Ugo M. Pagnoni; Ennio Valentin; Adele Mucci; Franco Bellesia

doi:10.1055/s-2008-1067273

Preparation of the Maleic Anhydride Nucleus from Dichloro gamma-Lactams: Focus on the Role of the N-Substituent in the Functional Rearrangement and in the Hydrolytic Steps

Franco Ghelfi, Mariella Pattarozzi, Fabrizio Roncaglia, Andrew F. Parsons, Fulvia Felluga, Ugo M. Pagnoni, Ennio Valentin, Adele Mucci, Franco Bellesia

Chemistry

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

Abstract

The preparation of the 3,4-dialkyl-substituted maleic anhydride nucleus, through the functional rearrangement of dichloro gamma-lactams, allowed the comparison of various N-substituents in the functional rearrangement step. The 2-pyridyl group proved to be the most appropriate N-substituent for the hydrolysis of the 5-methoxy-1,5-dihydro-2H-pyrrol-2-one intermediate into the 5-hydroxy adduct, and for the hydrolysis of the maleimide nucleus into the maleic anhydride. The oxidation of the 5-hydroxy-1,5-dihydro-2H-pyrrol-2-one into the corresponding maleimide was achieved with manganese(IV) oxide.

Original language	English
Article number	Z12108SS
Pages (from-to)	3131-3141
Number of pages	11
Journal	SYNTHESIS-STUTTGART
Issue number	19
DOIs	https://doi.org/10.1055/s-2008-1067273
Publication status	Published - 1 Oct 2008

Keywords

rearrangement
radical reactions
substituent effects
halo compounds
gamma-lactams
TRANSFER RADICAL CYCLIZATION
DIMETHYLMALEIC ANHYDRIDE
CHAETOMELLIC ANHYDRIDE
ACID
CONVERSION
MECHANISM
OXIDATION

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10.1055/s-2008-1067273

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Ghelfi, F., Pattarozzi, M., Roncaglia, F., Parsons, A. F., Felluga, F., Pagnoni, U. M., Valentin, E., Mucci, A., & Bellesia, F. (2008). Preparation of the Maleic Anhydride Nucleus from Dichloro gamma-Lactams: Focus on the Role of the N-Substituent in the Functional Rearrangement and in the Hydrolytic Steps. SYNTHESIS-STUTTGART, (19), 3131-3141. Article Z12108SS. https://doi.org/10.1055/s-2008-1067273

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title = "Preparation of the Maleic Anhydride Nucleus from Dichloro gamma-Lactams: Focus on the Role of the N-Substituent in the Functional Rearrangement and in the Hydrolytic Steps",

abstract = "The preparation of the 3,4-dialkyl-substituted maleic anhydride nucleus, through the functional rearrangement of dichloro gamma-lactams, allowed the comparison of various N-substituents in the functional rearrangement step. The 2-pyridyl group proved to be the most appropriate N-substituent for the hydrolysis of the 5-methoxy-1,5-dihydro-2H-pyrrol-2-one intermediate into the 5-hydroxy adduct, and for the hydrolysis of the maleimide nucleus into the maleic anhydride. The oxidation of the 5-hydroxy-1,5-dihydro-2H-pyrrol-2-one into the corresponding maleimide was achieved with manganese(IV) oxide.",

keywords = "rearrangement, radical reactions, substituent effects, halo compounds, gamma-lactams, TRANSFER RADICAL CYCLIZATION, DIMETHYLMALEIC ANHYDRIDE, CHAETOMELLIC ANHYDRIDE, ACID, CONVERSION, MECHANISM, OXIDATION",

author = "Franco Ghelfi and Mariella Pattarozzi and Fabrizio Roncaglia and Parsons, {Andrew F.} and Fulvia Felluga and Pagnoni, {Ugo M.} and Ennio Valentin and Adele Mucci and Franco Bellesia",

year = "2008",

month = oct,

day = "1",

doi = "10.1055/s-2008-1067273",

language = "English",

pages = "3131--3141",

journal = "SYNTHESIS-STUTTGART",

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Ghelfi, F, Pattarozzi, M, Roncaglia, F, Parsons, AF, Felluga, F, Pagnoni, UM, Valentin, E, Mucci, A & Bellesia, F 2008, 'Preparation of the Maleic Anhydride Nucleus from Dichloro gamma-Lactams: Focus on the Role of the N-Substituent in the Functional Rearrangement and in the Hydrolytic Steps', SYNTHESIS-STUTTGART, no. 19, Z12108SS, pp. 3131-3141. https://doi.org/10.1055/s-2008-1067273

Preparation of the Maleic Anhydride Nucleus from Dichloro gamma-Lactams: Focus on the Role of the N-Substituent in the Functional Rearrangement and in the Hydrolytic Steps. / Ghelfi, Franco; Pattarozzi, Mariella; Roncaglia, Fabrizio et al.
In: SYNTHESIS-STUTTGART, No. 19, Z12108SS, 01.10.2008, p. 3131-3141.

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

TY - JOUR

T1 - Preparation of the Maleic Anhydride Nucleus from Dichloro gamma-Lactams: Focus on the Role of the N-Substituent in the Functional Rearrangement and in the Hydrolytic Steps

AU - Ghelfi, Franco

AU - Pattarozzi, Mariella

AU - Roncaglia, Fabrizio

AU - Parsons, Andrew F.

AU - Felluga, Fulvia

AU - Pagnoni, Ugo M.

AU - Valentin, Ennio

AU - Mucci, Adele

AU - Bellesia, Franco

PY - 2008/10/1

Y1 - 2008/10/1

N2 - The preparation of the 3,4-dialkyl-substituted maleic anhydride nucleus, through the functional rearrangement of dichloro gamma-lactams, allowed the comparison of various N-substituents in the functional rearrangement step. The 2-pyridyl group proved to be the most appropriate N-substituent for the hydrolysis of the 5-methoxy-1,5-dihydro-2H-pyrrol-2-one intermediate into the 5-hydroxy adduct, and for the hydrolysis of the maleimide nucleus into the maleic anhydride. The oxidation of the 5-hydroxy-1,5-dihydro-2H-pyrrol-2-one into the corresponding maleimide was achieved with manganese(IV) oxide.

AB - The preparation of the 3,4-dialkyl-substituted maleic anhydride nucleus, through the functional rearrangement of dichloro gamma-lactams, allowed the comparison of various N-substituents in the functional rearrangement step. The 2-pyridyl group proved to be the most appropriate N-substituent for the hydrolysis of the 5-methoxy-1,5-dihydro-2H-pyrrol-2-one intermediate into the 5-hydroxy adduct, and for the hydrolysis of the maleimide nucleus into the maleic anhydride. The oxidation of the 5-hydroxy-1,5-dihydro-2H-pyrrol-2-one into the corresponding maleimide was achieved with manganese(IV) oxide.

KW - rearrangement

KW - radical reactions

KW - substituent effects

KW - halo compounds

KW - gamma-lactams

KW - TRANSFER RADICAL CYCLIZATION

KW - DIMETHYLMALEIC ANHYDRIDE

KW - CHAETOMELLIC ANHYDRIDE

KW - ACID

KW - CONVERSION

KW - MECHANISM

KW - OXIDATION

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U2 - 10.1055/s-2008-1067273

DO - 10.1055/s-2008-1067273

M3 - Article

SN - 0039-7881

SP - 3131

EP - 3141

JO - SYNTHESIS-STUTTGART

JF - SYNTHESIS-STUTTGART

IS - 19

M1 - Z12108SS

ER -

Preparation of the Maleic Anhydride Nucleus from Dichloro gamma-Lactams: Focus on the Role of the N-Substituent in the Functional Rearrangement and in the Hydrolytic Steps

Abstract

Keywords

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