A Novel Ylide-stabilized Carbene; Formation and Electron Donating Ability of an Amino(sulfur-ylide)carbene

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2008 Dec 17

PMID 19082130

Citations 5

Authors

Junji Kobayashi

Shin-ya Nakafuji

Atsushi Yatabe

Takayuki Kawashima

Affiliations

Soon will be listed here.

Abstract

A novel N-heterocyclic carbene, amino(sulfur-ylide)carbene, which is stabilized by electron donation from the carbanion of a sulfur ylide as well as a nitrogen atom, was generated and its Rh complex was synthesized; the electron donating properties of the amino(sulfur-ylide)carbene were investigated using the IR carbonyl stretching frequencies of the Rh complex, indicating a relatively strong electron-donating ability among reported carbenes.

Citing Articles

Phosphorus-ylides: powerful substituents for the stabilization of reactive main group compounds.

Sarbajna A, Swamy V, Gessner V Chem Sci. 2021; 12(6):2016-2024.

PMID: 34163963 PMC: 8179322. DOI: 10.1039/d0sc03278f.

A 2,2'-diphosphinotolane as a versatile precursor for the synthesis of P-ylidic mesoionic carbenes reversible C-P bond formation.

Wagner H, Wadepohl H, Ballmann J Chem Sci. 2021; 12(10):3693-3701.

PMID: 34163643 PMC: 8179451. DOI: 10.1039/d0sc06128j.

Taming the Antiferromagnetic Beast: Computational Design of Ultrashort Mn-Mn Bonds Stabilized by N-Heterocyclic Carbenes.

Francisco M, Fantuzzi F, Cardozo T, Esteves P, Engels B, Oliveira R Chemistry. 2021; 27(47):12126-12136.

PMID: 34114702 PMC: 8456913. DOI: 10.1002/chem.202101116.

Towards the Preparation of Stable Cyclic Amino(ylide)Carbenes.

Steinert H, Schwarz C, Kroll A, Gessner V Molecules. 2020; 25(4).

PMID: 32059503 PMC: 7070660. DOI: 10.3390/molecules25040796.

Stable cyclic carbenes and related species beyond diaminocarbenes.

Melaimi M, Soleilhavoup M, Bertrand G Angew Chem Int Ed Engl. 2010; 49(47):8810-49.

PMID: 20836099 PMC: 3130005. DOI: 10.1002/anie.201000165.