Radical aminomethylation of unactivated alkenes

Béatrice Quiclet-Sire; Samir Z. Zard

doi:10.1021/ol801162m

Radical aminomethylation of unactivated alkenes

Béatrice Quiclet-Sire
, Samir Z. Zard

Laboratoire de Synthèse Organique

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

59 Citations (Scopus)

Résumé

(Chemical Equation Presented) S-Succinimidomethyl- and S-phthalimidomethyl xanthates are added efficiently to various alkenes resulting in an overall aminomethylation process. In contrast, under similar conditions, S-pyrrolidonyl xanthate gives rise mostly to oligomers. This unexpected difference in reactivity is attributed to the more important allylic character of the intermediate radical in the case of the imide derivative as compared to the lactam.

langue originale	Anglais
Pages (de - à)	3279-3282
Nombre de pages	4
journal	Organic Letters
Volume	10
Numéro de publication	15
Les DOIs	https://doi.org/10.1021/ol801162m
état	Publié - 1 déc. 2008
Modification externe	Oui

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10.1021/ol801162m

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title = "Radical aminomethylation of unactivated alkenes",

abstract = "(Chemical Equation Presented) S-Succinimidomethyl- and S-phthalimidomethyl xanthates are added efficiently to various alkenes resulting in an overall aminomethylation process. In contrast, under similar conditions, S-pyrrolidonyl xanthate gives rise mostly to oligomers. This unexpected difference in reactivity is attributed to the more important allylic character of the intermediate radical in the case of the imide derivative as compared to the lactam.",

author = "B{\'e}atrice Quiclet-Sire and Zard, \{Samir Z.\}",

year = "2008",

month = dec,

day = "1",

doi = "10.1021/ol801162m",

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journal = "Organic Letters",

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T1 - Radical aminomethylation of unactivated alkenes

AU - Quiclet-Sire, Béatrice

AU - Zard, Samir Z.

PY - 2008/12/1

Y1 - 2008/12/1

N2 - (Chemical Equation Presented) S-Succinimidomethyl- and S-phthalimidomethyl xanthates are added efficiently to various alkenes resulting in an overall aminomethylation process. In contrast, under similar conditions, S-pyrrolidonyl xanthate gives rise mostly to oligomers. This unexpected difference in reactivity is attributed to the more important allylic character of the intermediate radical in the case of the imide derivative as compared to the lactam.

AB - (Chemical Equation Presented) S-Succinimidomethyl- and S-phthalimidomethyl xanthates are added efficiently to various alkenes resulting in an overall aminomethylation process. In contrast, under similar conditions, S-pyrrolidonyl xanthate gives rise mostly to oligomers. This unexpected difference in reactivity is attributed to the more important allylic character of the intermediate radical in the case of the imide derivative as compared to the lactam.

U2 - 10.1021/ol801162m

DO - 10.1021/ol801162m

M3 - Article

AN - SCOPUS:59949101791

SN - 1523-7060

VL - 10

SP - 3279

EP - 3282

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Radical aminomethylation of unactivated alkenes

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