Reinvestigation of Reaction of (2-Ethoxyvinyl)stannanes with Acetyl Bromide

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Title:Reinvestigation of Reaction of (2-Ethoxyvinyl)stannanes with Acetyl Bromide
Creators:
Lébl, Tomáš
Holeček, Jaroslav
Dymák, Marek
Steinborn, Dirk
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 5, pp. 587-595
Uncontrolled Keywords:Tin-carbon bond cleavage, Kinetics, Stannanes, Heterolytic fragmentation, Tin, Reaction mechanisms, NMR spectroscopy

Abstract

Four analogous (2-ethoxyvinyl)stannanes (<i>E/Z</i>)-Bu<sub>3</sub>SnC(R)=CHOEt (R = Bu, H) were prepared and characterised using <sup>1</sup>H, <sup>13</sup>C, <sup>119</sup>Sn, <sup>1</sup>H-<sup>13</sup>C HMQC, <sup>1</sup>H-<sup>13</sup>C HMBC, and <sup>1</sup>H-<sup>119</sup>Sn HMQC NMR spectroscopy. The course of their reactions with acetyl bromide was studied by NMR spectroscopy. Although tributyltin bromide, ethyl acetate and the coresponding alkyne were identified as reaction products, this present reinvestigation showed unambiguously that heterolytic fragementation reactions, as stated previously, did not take place. Acetyl bromide cleaves the Sn-C= bond yielding tributyltin bromide and vinyl ethers. Subsequent decomposition of vinyl ethers and impurities in the starting stannane is the source of ethyl acetate and the alkyne, respectively. <p>

Title:Reinvestigation of Reaction of (2-Ethoxyvinyl)stannanes with Acetyl Bromide
Creators:
Lébl, Tomáš
Holeček, Jaroslav
Dymák, Marek
Steinborn, Dirk
Uncontrolled Keywords:Tin-carbon bond cleavage, Kinetics, Stannanes, Heterolytic fragmentation, Tin, Reaction mechanisms, NMR spectroscopy
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:67
Number:5
Page Range:pp. 587-595
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20020587UNSPECIFIED
ID Code:1944
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Lébl, Tomáš; Holeček, Jaroslav; Dymák, Marek; Steinborn, Dirk (2002) Reinvestigation of Reaction of (2-Ethoxyvinyl)stannanes with Acetyl Bromide. Collection of Czechoslovak Chemical Communications, 67 (5). pp. 587-595. ISSN 0010-0765

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