Individual Listing

PIERCE HALL
University of California
Riverside, CA 92521

Bertrand, Guy

Distinguished Professor

College of Natural and Agricultural Sciences

Chemistry


Biography

 

Awards

2006 American Association for the Advancement of Science, Chemistry
2004 French Academy of Science
2000 Elected at the French Academy of Technology
1999 Japanese Society for Promotion of Science Award
1998 Kharasch Lecturer, University of Chicago
1998 Médaille d'Argent du CNRS
1996 Elected at the French Academy of Sciences (Membre Correspondant)
1994 French-German Humboldt Award
1993 International Council on Main Group Chemistry Award


Research Area

We are dealing with main group elements from group 13 to 16, at the border between organic, organometallic and inorganic chemistry, with some developments in the field of polymers. We use the specific properties of main group elements, especially boron, silicon and phosphorus, to stabilize organic species, which are supposed to be only transient intermediates, such as carbenes, nitrenes, radicals and biradicals, 1,3-dipoles, anti-aromatic heterocycles... The following figure shows our latest stable carbene (mp: 16°C), which features a spectator substituent. Another main topic is the search of new types of bonding, which are unknown in classical organic chemistry. We use low lying s* orbitals to develop the concept of s*-aromaticity and anti-aromaticity. The synthesis of the first compounds featuring one electron phosphorus-phosphorus bonds, resulting from p*-p* interaction is a good illustration of our approach. This compound can also be considered as a new type of benzene valence isomer (more precisely, a tetraphosphabenzene valence isomer). The peculiar design of our molecules gives rise to original properties. For example, we recently prepared a series of Lewis acids, which are extremely efficient catalysts for ring opening polymerization; by this route, we prepare biocompatible polymers to encapsulate pharmaceutical drugs.

Publications

Singlet Diradicals: From Transition States to Crystalline Compounds
David Scheschkewitz, Hideki Amii, Heinz Gornitzka, Wolfgang W. Schoeller, Didier Bourissou, Guy Bertrand
Science.

Amino-aryl-carbenes: stable singlet carbenes featuring a spectator substituent S. Solé, H. Gornitzka, W.W. Schoeller, D. Bourissou, G. Bertrand
Science, 292, 1901-1903 (2001)
See also Science 292, 1846 (2001)

On the electronic structure of (phosphino)(silyl) carbenes : single crystal X-ray diffraction and ELF analyses
T. Kato, H. Gornitzka, A. Baceiredo, A. Savin, G. Bertrand
J. Am. Chem. Soc., 122, 998-999

Stable versions of transient push-pull carbenes: extending lifetimes from nanoseconds to weeks.
C. Buron, H. Gornitzka, V. Romanenko, G. Bertrand
Science, 288, 834-836 (2000)

Stereo-selectivity and -specificity of cyclopropanation reactions with stable (phosphanyl)(silyl)carbenes.
S. Goumri-Magnet, T. Kato, H. Gornitzka, A. Baceiredo, G. Bertrand
J. Am. Chem. Soc., 122, 4464-4470 (2000)

A cyclic carbanionic valence isomer of a carbocation: diphosphino analogs of diaminocarbocations
T. Kato, H. Gornitzka, A. Baceiredo, W.W. Schoeller, G. Bertrand
Science, 289, 754-756 (2000) See also Science 289, 737 (2000)

Synthesis, structure and reactivity of a 1s4,3s2-diphosphaallene
T. Kato, H. Gornitzka, A. Baceiredo, G. Bertrand
Angew. Chem. Int. Ed. Engl., 39, 3319-3321 (2000)

Stable carbenes
D. Bourissou, O. Guerret, F. Gabbaï, G. Bertrand
Chem. Rev. 100, 39-92 (2000)

Synthetic utility of stable phosphinocarbenes: preparation and X-ray crystal structure of an a-(lithiomethylene)phosphorane
S. Goumri-Magnet, H. Gornitzka, A. Baceiredo, G. Bertrand
Angew. Chem. Int. Ed. Engl., 38, 678-680 (1999)

The quest for diphosphirenium and diphosphirenylium salts. Diheteroatom-containing cyclopropenium analogues
D. Bourissou, G. Bertrand
Acc. Chem. Res., 32, 561-570 (1999)

New types of stable aldehydes: formylphosphane and formylphosphane oxide
D. Amsallem, H. Gornitzka, A. Baceiredo, G. Bertrand
Angew. Chem. Int. Ed. Engl., 38, 2201-2203 (1999)

The electrophilic behavior of stable phosphinocarbenes towards phosphorus lone pairs
S. Goumri-Magnet, O. Polischuck, H. Gornitzka, A. Baceiredo, G. Bertrand
Angew. Chem. Int. Ed. Engl., 38, 3727-3729 (1999)

Isolation of a benzene valence isomer with one-electron phosphorus-phosphorus bonds
Y. Canac, D. Bourissou, A. Baceiredo, H. Gornitzka, W.W. Schoeller, G. Bertrand
Science, 279, 2080-2082 (1998)

Ylidic four p-electron four-membered l5-phosphorus heterocycles : electronical isomers of heterocyclobutadienes
G. Bertrand
Angew. Chem. Int. Ed. Engl., 37, 270-281 (1998)

The azide-nitrilimine analogy in aluminum chemistry
N. Emig, F. Gabbaï, H. Krautscheid, R. Réau, G. Bertrand
Angew. Chem. Int. Ed. Engl., 37, 989-992 (1998)

1,2-Silyl migrations for aromatic carbenes: a specific pathway
S. Solé, H. Gornitzka, O. Guerret, G. Bertrand
J. Am. Chem. Soc., 120, 9100-9101 (1998)