Regioselective hydrosilylation-desilylation: convenient preparation of a 2-(trimethylsilyl)-1-alkene

Hudrlik, Paul F.; Schwartz, Robert H.; Hogan, J. C.

doi:10.1021/jo01315a040

Cited by 34 publications

(5 citation statements)

References 1 publication

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“…The reaction mechanisms of the hydrolysis−desilylation of vinylsilanes have been studied . Retention of configurations has been generally obtained .…”

Section: Resultsmentioning

confidence: 99%

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Preparation of Partially Substituted 1-Halo- and 1,4-Dihalo-1,3-dienes via Reagent-Controlled Desilylation of Halogenated 1,3-Dienes

Song

Liu

et al. 2006

J. Org. Chem.

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Depending on the desilylation reagents used, 1-halo-1,4-bis(trimethylsilyl)-1,3-butadienes afforded either 1-halo-1-trimethylsilyl-1,3-butadienes or 1-halo-4-trimethylsilyl-1,3-butadienes in excellent yields with excellent selectivity, respectively, when treated with CF3COOH or with NaOMe. These monosilylated 1,3-butadiene products could be further desilylated to generate their corresponding halobutadienes via the above reagent-controlled desilylation reaction. When 1,4-dihalo-1,4-bis(trimethylsilyl)-1,3-dienes were treated with MeONa/MeOH at room temperature, desilylation of both of the two trimethylsilyl groups took place to afford their corresponding 1,4-dihalo-1,3-dienes in excellent yields. The commonly used desilylation reagent CF3COOH did not work for these dihalobutadienes.

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“…The reaction mechanisms of the hydrolysis−desilylation of vinylsilanes have been studied . Retention of configurations has been generally obtained .…”

Section: Resultsmentioning

confidence: 99%

“…The reaction mechanisms of the hydrolysis−desilylation of vinylsilanes have been studied . Retention of configurations has been generally obtained . In the case of CF 3 COOH-promoted protonation−desilylation, an electrophilic substitution reaction is involved.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Partially Substituted 1-Halo- and 1,4-Dihalo-1,3-dienes via Reagent-Controlled Desilylation of Halogenated 1,3-Dienes

Song

Liu

et al. 2006

J. Org. Chem.

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“…The use of [02H]-p-toluenesulfinic acid 5) smoothly effected the desilylation, but caused randomization of the label (E: Z, 2.3: 1, 70% deuteration). The problem was finally solved by the use of [02H]acetic acid 6 ) under reflux for 48 h; 4 was successfully converted into (2E)-[3-2 H]-1-benzyloxy-2propene (6; E: Z, 100: 8).…”

Section: Sn-(3r)-[3-2 H]- Sn-(3s)-[3-2 H]- Si1-(ls)-[1-2h]-and Sn-(mentioning

confidence: 99%

Enantio- and Stereoselective Syntheses of Monodeuterium-labeled Glycerols

Yagi

Oikawa

Ichihara

1997

Bioscience, Biotechnology, and Biochemistry

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“…All the remaining compounds were synthesized according to literature methods: 3,,' 4,, ' 5,33 9,34 lo3' and ll. 35 All samples were freshly distilled prior to measurements and purified, if necessary, by gas chromatography.…”

Section: Synthesis Of Compoundsmentioning

confidence: 99%

Large CC spin–spin coupling constants across double bonds. Validity of the multiplicative approach

Kamieńska‐Trela¹,

Biedrzycka²,

Dąbrowski³

1991

Magnetic Reson in Chemistry

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Regioselective hydrosilylation-desilylation: convenient preparation of a 2-(trimethylsilyl)-1-alkene

Cited by 34 publications

References 1 publication

Preparation of Partially Substituted 1-Halo- and 1,4-Dihalo-1,3-dienes via Reagent-Controlled Desilylation of Halogenated 1,3-Dienes

Preparation of Partially Substituted 1-Halo- and 1,4-Dihalo-1,3-dienes via Reagent-Controlled Desilylation of Halogenated 1,3-Dienes

Enantio- and Stereoselective Syntheses of Monodeuterium-labeled Glycerols

Large CC spin–spin coupling constants across double bonds. Validity of the multiplicative approach

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