Stevens Rearrangement of Carbamoylaminimides

Richard F. Smith; Richard D. Blondell; Rebecca A. Abgott; Kenneth B. Lipkowitz; James A. Richmond; Keith A. Fountain

doi:10.1021/jo00928a012

Stevens Rearrangement of Carbamoylaminimides

Richard F. Smith
, Richard D. Blondell
, Rebecca A. Abgott
, Kenneth B. Lipkowitz
, James A. Richmond
, Keith A. Fountain

Family Medicine

SUNY Geneseo

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

10 Scopus citations

Abstract

Carbamoylaminimides (7) with 1-allyl and 1-benzyl substituents undergo thermal Stevens rearrangements to give semicarbazides (8). Thermolysis of 1-(3-methyl-2-butenyl)- and 1-(2-butenyl)aminimides (9 and 11) give products resulting from allyl retention, thus ruling out a concerted mechanism for the N₁ ⟶ N₂ allyl rearrangement.

Original language	English
Pages (from-to)	2036-2040
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	39
Issue number	14
DOIs	https://doi.org/10.1021/jo00928a012
State	Published - Jul 1 1974

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title = "Stevens Rearrangement of Carbamoylaminimides",

abstract = "Carbamoylaminimides (7) with 1-allyl and 1-benzyl substituents undergo thermal Stevens rearrangements to give semicarbazides (8). Thermolysis of 1-(3-methyl-2-butenyl)- and 1-(2-butenyl)aminimides (9 and 11) give products resulting from allyl retention, thus ruling out a concerted mechanism for the N1 ⟶ N2 allyl rearrangement.",

author = "Smith, \{Richard F.\} and Blondell, \{Richard D.\} and Abgott, \{Rebecca A.\} and Lipkowitz, \{Kenneth B.\} and Richmond, \{James A.\} and Fountain, \{Keith A.\}",

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T1 - Stevens Rearrangement of Carbamoylaminimides

AU - Smith, Richard F.

AU - Blondell, Richard D.

AU - Abgott, Rebecca A.

AU - Lipkowitz, Kenneth B.

AU - Richmond, James A.

AU - Fountain, Keith A.

PY - 1974/7/1

Y1 - 1974/7/1

N2 - Carbamoylaminimides (7) with 1-allyl and 1-benzyl substituents undergo thermal Stevens rearrangements to give semicarbazides (8). Thermolysis of 1-(3-methyl-2-butenyl)- and 1-(2-butenyl)aminimides (9 and 11) give products resulting from allyl retention, thus ruling out a concerted mechanism for the N1 ⟶ N2 allyl rearrangement.

AB - Carbamoylaminimides (7) with 1-allyl and 1-benzyl substituents undergo thermal Stevens rearrangements to give semicarbazides (8). Thermolysis of 1-(3-methyl-2-butenyl)- and 1-(2-butenyl)aminimides (9 and 11) give products resulting from allyl retention, thus ruling out a concerted mechanism for the N1 ⟶ N2 allyl rearrangement.

UR - https://www.scopus.com/pages/publications/0005134798

U2 - 10.1021/jo00928a012

DO - 10.1021/jo00928a012

M3 - Article

AN - SCOPUS:0005134798

SN - 0022-3263

VL - 39

SP - 2036

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -

Stevens Rearrangement of Carbamoylaminimides

Abstract

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