What question did this study set out to answer?

To evaluate N-hydroxypyridine-2-thione carbamate derivatives as efficient precursors for generating aminyl and aminium radicals to construct pyrrolidine rings.

May 1, 1987Journal of the American Chemical Society

N-Hydroxypyridine-2-thione carbamates as aminyl and aminium radical precursors. Cyclizations for synthesis of the pyrrolidine nucleus

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Authors

MNMartin NewcombAdvanced Coatings (Belgium)TDThomas M. DeebTexas A&M University

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Implication

Experimental study demonstrates radical cyclizations using N-hydroxypyridine-2-thione carbamates to generate aminyl intermediates, indicating a novel pathway for pyrrolidine synthesis.

Key Points

To evaluate N-hydroxypyridine-2-thione carbamate derivatives as efficient precursors for generating aminyl and aminium radicals to construct pyrrolidine rings.
Synthesized N-hydroxypyridine-2-thione carbamate derivatives designed to liberate nitrogen-centered radical species upon activation.
Conducted intramolecular cyclization reactions of the generated aminyl and aminium radical intermediates targeting the pyrrolidine core.
Confirmed that N-hydroxypyridine-2-thione carbamates serve as competent precursors for generating neutral aminyl and positively charged aminium radicals.
Achieved successful radical cyclization pathways leading to the formation of the pyrrolidine nucleus.

Cite This Study

Newcomb et al. (1987) studied this question.

synapsesocial.com/papers/6a8199e45d6bc1011b4cd63a https://doi.org/10.1021/ja00244a060

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Implication

Experimental study demonstrates radical cyclizations using N-hydroxypyridine-2-thione carbamates to generate aminyl intermediates, indicating a novel pathway for pyrrolidine synthesis.

N-Hydroxypyridine-2-thione carbamates as aminyl and aminium radical precursors. Cyclizations for synthesis of the pyrrolidine nucleus

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Implication

Key Points

Cite This Study

N-Hydroxypyridine-2-thione carbamates as aminyl and aminium radical precursors. Cyclizations for synthesis of the pyrrolidine nucleus

Discussion

Member takes

Implication

Key Points

Cite This Study

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