Alkylidenecarbene insertion into a nitrogen lone pair: An unexpected synthesis of dihydropyrroles from alkynyliodonium salts

Ken S. Feldman; Pamela A. Mingo; Paul C.D. Hawkins

doi:10.3987/com-99-8481

Alkylidenecarbene insertion into a nitrogen lone pair: An unexpected synthesis of dihydropyrroles from alkynyliodonium salts

Ken S. Feldman, Pamela A. Mingo, Paul C.D. Hawkins

Chemistry

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

19 Scopus citations

Abstract

A novel intramolecular reaction between an alkylidenecarbene and the lone pair of electrons on a carbamate's nitrogen is described. The reaction occurs preferentially over an available 1,5 C-H insertion and gives substituted dihydropyrroles upon workup.

Original language	English (US)
Pages (from-to)	1283-1294
Number of pages	12
Journal	Heterocycles
Volume	51
Issue number	6
DOIs	https://doi.org/10.3987/com-99-8481
State	Published - Jun 1 1999

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Alkylidenecarbene insertion into a nitrogen lone pair: An unexpected synthesis of dihydropyrroles from alkynyliodonium salts",

abstract = "A novel intramolecular reaction between an alkylidenecarbene and the lone pair of electrons on a carbamate's nitrogen is described. The reaction occurs preferentially over an available 1,5 C-H insertion and gives substituted dihydropyrroles upon workup.",

author = "Feldman, \{Ken S.\} and Mingo, \{Pamela A.\} and Hawkins, \{Paul C.D.\}",

year = "1999",

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T2 - An unexpected synthesis of dihydropyrroles from alkynyliodonium salts

AU - Feldman, Ken S.

AU - Mingo, Pamela A.

AU - Hawkins, Paul C.D.

PY - 1999/6/1

Y1 - 1999/6/1

N2 - A novel intramolecular reaction between an alkylidenecarbene and the lone pair of electrons on a carbamate's nitrogen is described. The reaction occurs preferentially over an available 1,5 C-H insertion and gives substituted dihydropyrroles upon workup.

AB - A novel intramolecular reaction between an alkylidenecarbene and the lone pair of electrons on a carbamate's nitrogen is described. The reaction occurs preferentially over an available 1,5 C-H insertion and gives substituted dihydropyrroles upon workup.

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U2 - 10.3987/com-99-8481

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M3 - Article

AN - SCOPUS:0033150474

SN - 0385-5414

VL - 51

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JO - Heterocycles

JF - Heterocycles

IS - 6

ER -

Alkylidenecarbene insertion into a nitrogen lone pair: An unexpected synthesis of dihydropyrroles from alkynyliodonium salts

Abstract

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