+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ PDF Full Text
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Translate
+ Recently Requested

Oxidative Addition of Disulfides, Alkyl Sulfides, and Diphosphides to an Aluminum(I) Center

Oxidative Addition of Disulfides, Alkyl Sulfides, and Diphosphides to an Aluminum(I) Center

Inorganic Chemistry 55(17): 9099-9104

The aluminum(I) compound NacNacAl (1) reacts with diphenyl disulfide and diethyl sulfide to form the respective four-coordinate bis(phenyl sulfide) complex NacNacAl(SPh)2 (2) and alkyl thiolate aluminum complex NacNacAlEt(SEt) (3). As well, reaction of 1 with tetraphenyl diphosphine furnishes the bis(diphenyl phosphido) complex NacNacAl(PPh2)2 (4). Production of 3 and 4 are the first examples of C(sp(3))-S and R2P-PR2 activation by a main-group element complex. All three complexes were characterized by multinuclear NMR spectroscopy and X-ray crystal structure analysis. Furthermore, a variable-temperature NMR spectroscopic study was undertaken on 4 to study its dynamic behavior in solution.

(PDF emailed within 0-6 h: $19.90)

Accession: 058488369

Download citation: RISBibTeXText

PMID: 27529564

DOI: 10.1021/acs.inorgchem.6b01668

Related references

Reactivity of tert-butoxy radicals towards thiols, alkyl sulfides, and alkyl disulfides. International Journal of Chemical Kinetics 21(4): 245-250, 1989

Oxidative Cleavage of C=S and P=S Bonds at an Al I Center: Preparation of Terminally Bound Aluminum Sulfides. Angewandte Chemie 55(42): 13306-13311, 2016

One-Pot Synthesis of Sulfides by Reaction of Disulfides with Alkyl Halides in the Presence of Sodium Dithionite. Phosphorus Sulfur and Silicon and the Related Elements 182(1): 167-174, 2007

Aziridine sulfides and disulfides as catalysts for the enantioselective addition of diethylzinc to aldehydes. Chemical Communications: 2488-2489, 2004

Oxidation of organic sulfides and disulfides with atert-butyl hydroperoxide-aluminum tri-tert-butoxide system. Russian Chemical Bulletin 60(1): 185-187, 2011

Synthesis of 2-chloroethyl alkyl sulfones by the oxidative chlorination of 2-hydroxyethyl alkyl sulfides. Russian Chemical Bulletin 25(4): 919-921, 1976

Experimental and theoretical studies of the reaction of the OH radical with alkyl sulfides: 3. Kinetics and mechanism of the OH initiated oxidation of dimethyl, dipropyl, and dibutyl sulfides: reactivity trends in the alkyl sulfides and development of a predictive expression for the reaction of OH with DMS. Journal of Physical Chemistry. A 113(24): 6697-6709, 2009

Indium(I) iodide-promoted cleavage of diaryl diselenides and disulfides and subsequent condensation with alkyl or acyl halides. One-pot efficient synthesis of diorganyl selenides, sulfides, selenoesters, and thioesters. Journal of Organic Chemistry 69(17): 5793-5795, 2004

Trimethylphenylammonium Tribromide as a New and Efficient Oxidizing Agent for the Oxidative Coupling of Thiols into Disulfides and Chemoselective Oxidation of Sulfides into Sulfoxides. Phosphorus Sulfur and Silicon and the Related Elements 186(8): 1665-1672, 2011

Functional sulfur-containing compounds 2. Synthesis of 3-chloropropyl and 4-chlorobutyl alkyl (phenyl) sulfones by the oxidative chlorination of 3-hydroxypropyl and 4-hydroxybutyl alkyl(phenyl) sulfides and sulfoxides. Russian Chemical Bulletin 27(9): 1823-1829, 1978

Oxidative chlorination of 2,3-epoxypropyl alkyl sulfides. Russian Chemical Bulletin 28(11): 2474-2474, 1979

Bimetallic oxidative addition involving radical intermediates in nickel-catalyzed alkyl-alkyl Kumada coupling reactions. Journal of the American Chemical Society 135(32): 12004-12012, 2013

Inhibitory effect of 2-(E-2-alkenoylamino)ethyl alkyl sulfides on gastric ulceration in rats. II. Structure and activity relationships of 2-(E-n or Z-n-Decenoylamino)ethyl alkyl sulfides. Chemical & Pharmaceutical Bulletin 39(6): 1546-1550, 1991

Preparation of Alkyl Ethynyl Sulfides and Alkyl E-2-Iodoethenyl Sulfides. Synthetic Communications 22(10): 1473-1479, 1992

Molecular vibrations and force fields of alkyl sulfides: Part XV. C-S stretching vibrations of aliphatic alkyl sulfides. Journal of Molecular Structure 42: 31-36, 1977