On the Mechanism of the Conversion of β/Iodo Carbamates to Aziridines

Alfred Hassner; Clayton Heathcock

doi:10.1021/jo01035a052

On the Mechanism of the Conversion of β/Iodo Carbamates to Aziridines

Alfred Hassner
, Clayton Heathcock

University of Colorado Boulder

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

21 Scopus citations

Abstract

The facile conversion of β/iodo carbamates with strong base to aziridines is shown to proceed via an intermediate N-carboalkoxy aziridine. The kinetics of the cyclization indicate abstraction of the proton from the carbamate nitrogen followed by a rate-determining ring closure made possible by neighboring group participation. Differences in rate of cyclization are explained on conformational grounds.

Original language	English
Pages (from-to)	3640-3645
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	29
Issue number	12
DOIs	https://doi.org/10.1021/jo01035a052
State	Published - 1 Dec 1964
Externally published	Yes

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10.1021/jo01035a052

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title = "On the Mechanism of the Conversion of β/Iodo Carbamates to Aziridines",

abstract = "The facile conversion of β/iodo carbamates with strong base to aziridines is shown to proceed via an intermediate N-carboalkoxy aziridine. The kinetics of the cyclization indicate abstraction of the proton from the carbamate nitrogen followed by a rate-determining ring closure made possible by neighboring group participation. Differences in rate of cyclization are explained on conformational grounds.",

author = "Alfred Hassner and Clayton Heathcock",

year = "1964",

month = dec,

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N2 - The facile conversion of β/iodo carbamates with strong base to aziridines is shown to proceed via an intermediate N-carboalkoxy aziridine. The kinetics of the cyclization indicate abstraction of the proton from the carbamate nitrogen followed by a rate-determining ring closure made possible by neighboring group participation. Differences in rate of cyclization are explained on conformational grounds.

AB - The facile conversion of β/iodo carbamates with strong base to aziridines is shown to proceed via an intermediate N-carboalkoxy aziridine. The kinetics of the cyclization indicate abstraction of the proton from the carbamate nitrogen followed by a rate-determining ring closure made possible by neighboring group participation. Differences in rate of cyclization are explained on conformational grounds.

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JF - Journal of Organic Chemistry

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On the Mechanism of the Conversion of β/Iodo Carbamates to Aziridines

Abstract

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