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

Research output: Contribution to journalArticle

19 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)1283-1294
Number of pages12
JournalHeterocycles
Volume51
Issue number6
StatePublished - Jun 1 1999

Fingerprint

Carbamates
Nitrogen
Salts
Electrons
pyrroline

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Feldman, Ken S. ; Mingo, Pamela A. ; Hawkins, Paul C.D. / Alkylidenecarbene insertion into a nitrogen lone pair : An unexpected synthesis of dihydropyrroles from alkynyliodonium salts. In: Heterocycles. 1999 ; Vol. 51, No. 6. pp. 1283-1294.
@article{71b57f7c72aa4997bb7bb61df85f35d4,
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",
month = "6",
day = "1",
language = "English (US)",
volume = "51",
pages = "1283--1294",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "6",

}

Alkylidenecarbene insertion into a nitrogen lone pair : An unexpected synthesis of dihydropyrroles from alkynyliodonium salts. / Feldman, Ken S.; Mingo, Pamela A.; Hawkins, Paul C.D.

In: Heterocycles, Vol. 51, No. 6, 01.06.1999, p. 1283-1294.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Alkylidenecarbene insertion into a nitrogen lone pair

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.

UR - http://www.scopus.com/inward/record.url?scp=0033150474&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033150474&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0033150474

VL - 51

SP - 1283

EP - 1294

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 6

ER -