Organometallic reactions in aqueous media — Antimony-mediated allylation of carbonyl compounds and the nature of allylstibine intermediates

2001 ◽  
Vol 79 (11) ◽  
pp. 1536-1540
Author(s):  
Lian-Hai Li ◽  
Tak Hang Chan
Keyword(s):  
Carbonyl Compounds ◽  
Good Yield ◽  
Allyl Bromide ◽  
Aqueous Media ◽  
Organometallic Reactions ◽  
Homoallylic Alcohols ◽  
Reaction Proceeds

Commercial antimony metal, in aqueous 1 M H(D)Cl solution, reacts with allyl bromide and aldehydes to give the corresponding homoallylic alcohols in good yield. The reaction proceeds through the formation of allylstibine intermediates. The structures of the allylstibine intermediates are likely to be allylstibine dibromide and diallylstibine bromide.Key words: allylation reaction, aqueous organometallic reactions, homoallylic alcohols, allylstibine dibromide, diallylstibine bromide.

ChemInform Abstract: Organometallic Reactions in Aqueous Media. The Nature of the Organotin Intermediate in the Tin-Mediated Allylation of Carbonyl Compounds.

ChemInform ◽  
2010 ◽  
Vol 30 (41) ◽  
pp. no-no
Author(s):  
Tak Hang Chan ◽  
Yang Yang ◽  
Chao Jun Li
Keyword(s):  
Carbonyl Compounds ◽  
Aqueous Media ◽  
Organometallic Reactions

ChemInform Abstract: Organometallic Reactions in Aqueous Media. Indium-Mediated 1,3-Butadien-2-ylation of Carbonyl Compounds.

ChemInform ◽  
2001 ◽  
Vol 32 (12) ◽  
pp. no-no
Author(s):  
Wenshuo Lu ◽  
Jihai Ma ◽  
Yang Yang ◽  
Tak Hang Chan
Keyword(s):  
Carbonyl Compounds ◽  
Aqueous Media ◽  
Organometallic Reactions

Organometallic Reactions in Aqueous Media: The Allylations of Carbonyl Compounds Mediated in Zn/CdSO4 and Zn/SnCl2 Bimetal Systems.

ChemInform ◽  
2004 ◽  
Vol 35 (43) ◽  
Author(s):  
Cunliu Zhou ◽  
Yuqing Zhou ◽  
Jiaoyang Jiang ◽  
Zhen Xie ◽  
Zhiyong Wang ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Aqueous Media ◽  
Organometallic Reactions

Organometallic reactions in aqueous media. Antimony-mediated allylation of carbonyl compounds with fluoride salts

2000 ◽  
Vol 41 (26) ◽  
pp. 5009-5012 ◽  
Author(s):  
Lian-Hai Li ◽  
Tak Hang Chan
Keyword(s):  
Carbonyl Compounds ◽  
Aqueous Media ◽  
Organometallic Reactions ◽  
Fluoride Salts

scholarly journals Comparative Studies on Conventional and Ultrasound-Assisted Synthesis of Novel Homoallylic Alcohol Derivatives Linked to Sulfonyl Dibenzene Moiety in Aqueous Media

2013 ◽  
Vol 2013 ◽  
pp. 1-9 ◽  
Author(s):  
Mohamed F. Mady ◽  
Ahmed A. El-Kateb ◽  
Ibrahim F. Zeid ◽  
Kåre B. Jørgensen
Keyword(s):  
Spectral Data ◽  
Comparative Studies ◽  
Carbonyl Compounds ◽  
Aqueous Media ◽  
Reaction Times ◽  
Ultrasound Irradiation ◽  
Reaction Conditions ◽  
Homoallylic Alcohols ◽  
Ultrasound Assisted ◽  
High Yields

Novel homoallylic alcohols incorporating sulfone moieties were synthesized by the treatment of different carbonyl compounds with allylic bromides in aqueous mediaviasonochemical Barbier-type reaction conditions. Sulfonation ofα-bromoketones with sodium benzenesulfinate in presence of CuI/2,6-lutidine rapidly gaveβ-keto-sulfones in good yields. In general, ultrasound irradiation offered the advantages of high yields, short reaction times, and simplicity compared to the conventional methods. The structures of all the compounds were confirmed by analytical and spectral data.

1993 R.U. Lemieux Award Lecture Organometallic-type reactions in aqueous media—a new challenge in organic synthesis

1994 ◽  
Vol 72 (5) ◽  
pp. 1181-1192 ◽  
Author(s):  
T.H. Chan ◽  
C.J. Li ◽  
M.C. Lee ◽  
Z.Y. Wei
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Organic Solvents ◽  
Carbonyl Compounds ◽  
Aqueous Media ◽  
Coupling Reactions ◽  
Homoallylic Alcohols ◽  
Allyl Halides ◽  
Nonulosonic Acid

The development of organometallic-type reactions in aqueous media is reviewed. Coupling reactions of allyl halides with carbonyl compounds mediated by zinc, or tin, or indium in aqueous media to give homoallylic alcohols are discussed. The stereochemical outcome is compared with similar reactions in organic solvents. A concise synthesis of (+)-muscarine is used to illustrate the usefulness of aqueous organometallic-type reactions in organic synthesis. The procedure to protect–deprotect hydroxy functional groups may not be necessary in these reactions. An application in the carbohydrate area is demonstrated with the synthesis of (+)-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). The mechanistic possibilities of organometallic-type reactions in aqueous media are outlined.

Organometallic reactions in aqueous media: the allylations of carbonyl compounds mediated in Zn/CdSO 4 and Zn/SnCl 2 bimetal systems

2004 ◽  
Vol 45 (28) ◽  
pp. 5537-5540 ◽  
Author(s):  
Cunliu Zhou ◽  
Yuqing Zhou ◽  
Jiaoyang Jiang ◽  
Zhen Xie ◽  
Zhiyong Wang ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Aqueous Media ◽  
Organometallic Reactions
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