Tetrahedron Letters

, volume 27 , issue 39 , pages 4763-4766

β-Halovinyl ketones: Synthesis from acetylenic ketones

MIKIO TANIGUCHI ¹

Shozo Kobayashi ¹

Masako NAKAGAWA ¹

Tohru HINO ¹

Y. Kishi ²

Hide authors affiliations Show authors affiliations: 2 affiliations

Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho Chiba, 260, Japan |

Department of Chemistry, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138 (USA) |

Publication type: Journal Article

Publication date: 1986-01-01

Elsevier

Tetrahedron Letters

scimago Q3

wos Q3

SJR: 0.334

CiteScore: 3.2

Impact factor: 1.5

ISSN: 00404039, 18733581

DOI: 10.1016/S0040-4039(00)85059-5

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

The reaction of terminal acetylenic ketones with NaI or LiBr gave almost exclusively E-β-iodo- or E-β-bromovinyl ketones in trifluoroacetic acid, while Z-β-iodo- or Z-β-bromovinyl ketones were the major products in acetic acid. Trimethylsilyl iodide and bromide reacted smoothly with acetylenic ketones at −78°C to give TMS-allenolates which were readily converted to β-iodo- and β-bromovinyl ketones, respectively. Practical syntheses of β-iodo- and β-bromovinyl ketones from the corresponding acetylenic ketones are described. The reaction of terminal acetylenic ketones with NaI or LiBr gave almost exclusively E-β-iodo- or E-β-bromovinyl ketones in TFA, while Z-β-iodo- or Z-B-bromovinyl ketones were the major products in AcOH.

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GOST |

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GOST Copy

TANIGUCHI M. et al. β-Halovinyl ketones: Synthesis from acetylenic ketones // Tetrahedron Letters. 1986. Vol. 27. No. 39. pp. 4763-4766.

GOST all authors (up to 50) Copy

TANIGUCHI M., Kobayashi S., NAKAGAWA M., HINO T., Kishi Y. β-Halovinyl ketones: Synthesis from acetylenic ketones // Tetrahedron Letters. 1986. Vol. 27. No. 39. pp. 4763-4766.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1016/S0040-4039(00)85059-5

UR - https://doi.org/10.1016/S0040-4039(00)85059-5

TI - β-Halovinyl ketones: Synthesis from acetylenic ketones

T2 - Tetrahedron Letters

AU - TANIGUCHI, MIKIO

AU - Kobayashi, Shozo

AU - NAKAGAWA, Masako

AU - HINO, Tohru

AU - Kishi, Y.

PY - 1986

DA - 1986/01/01

PB - Elsevier

SP - 4763-4766

IS - 39

VL - 27

SN - 0040-4039

SN - 1873-3581

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{1986_TANIGUCHI,

author = {MIKIO TANIGUCHI and Shozo Kobayashi and Masako NAKAGAWA and Tohru HINO and Y. Kishi},

title = {β-Halovinyl ketones: Synthesis from acetylenic ketones},

journal = {Tetrahedron Letters},

year = {1986},

volume = {27},

publisher = {Elsevier},

month = {jan},

url = {https://doi.org/10.1016/S0040-4039(00)85059-5},

number = {39},

pages = {4763--4766},

doi = {10.1016/S0040-4039(00)85059-5}

}

MLA

Cite this

MLA Copy

TANIGUCHI, MIKIO, et al. “β-Halovinyl ketones: Synthesis from acetylenic ketones.” Tetrahedron Letters, vol. 27, no. 39, Jan. 1986, pp. 4763-4766. https://doi.org/10.1016/S0040-4039(00)85059-5.

Publisher

Elsevier

Journal

Tetrahedron Letters

scimago Q3

wos Q3

SJR

0.334

CiteScore

3.2

Impact factor

1.5

ISSN

00404039 (Print)

18733581 (Electronic)