Direct formation of cyclobutenylphosphonates from 1-alkynylphosphonates and Cp2ZrCl2/2EtMgCl/2CuCl

Yulia Sinelnikove; Abraham Rubinstein; Morris Srebnik; Abed Al Aziz Al Quntar

doi:10.1016/j.tetlet.2008.11.108

Direct formation of cyclobutenylphosphonates from 1-alkynylphosphonates and Cp₂ZrCl₂/2EtMgCl/2CuCl

Yulia Sinelnikove
, Abraham Rubinstein
, Morris Srebnik^*
, Abed Al Aziz Al Quntar

^*Corresponding author for this work

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

Zirconacycles 2 prepared from 1-alkynylphosphonates 1, zirconocene dichloride, and 2 equiv of EtMgCl are smoothly converted into cyclobutenylphosphonates 3 when treated with two equiv of CuCl in 65-81% isolated yield. The reaction is specific and general only for zirconacyclopentenyl phosphonates.

Original language	English
Pages (from-to)	867-869
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2008.11.108
State	Published - 25 Feb 2009

Keywords

Alkynylphosphonates
Copper chloride
Cyclization
Cyclobutenylphosphonates
Diethylzirconocene

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10.1016/j.tetlet.2008.11.108

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title = "Direct formation of cyclobutenylphosphonates from 1-alkynylphosphonates and Cp2ZrCl2/2EtMgCl/2CuCl",

abstract = "Zirconacycles 2 prepared from 1-alkynylphosphonates 1, zirconocene dichloride, and 2 equiv of EtMgCl are smoothly converted into cyclobutenylphosphonates 3 when treated with two equiv of CuCl in 65-81\% isolated yield. The reaction is specific and general only for zirconacyclopentenyl phosphonates.",

keywords = "Alkynylphosphonates, Copper chloride, Cyclization, Cyclobutenylphosphonates, Diethylzirconocene",

author = "Yulia Sinelnikove and Abraham Rubinstein and Morris Srebnik and Quntar, \{Abed Al Aziz Al\}",

year = "2009",

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doi = "10.1016/j.tetlet.2008.11.108",

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T1 - Direct formation of cyclobutenylphosphonates from 1-alkynylphosphonates and Cp2ZrCl2/2EtMgCl/2CuCl

AU - Sinelnikove, Yulia

AU - Rubinstein, Abraham

AU - Srebnik, Morris

AU - Quntar, Abed Al Aziz Al

PY - 2009/2/25

Y1 - 2009/2/25

N2 - Zirconacycles 2 prepared from 1-alkynylphosphonates 1, zirconocene dichloride, and 2 equiv of EtMgCl are smoothly converted into cyclobutenylphosphonates 3 when treated with two equiv of CuCl in 65-81% isolated yield. The reaction is specific and general only for zirconacyclopentenyl phosphonates.

AB - Zirconacycles 2 prepared from 1-alkynylphosphonates 1, zirconocene dichloride, and 2 equiv of EtMgCl are smoothly converted into cyclobutenylphosphonates 3 when treated with two equiv of CuCl in 65-81% isolated yield. The reaction is specific and general only for zirconacyclopentenyl phosphonates.

KW - Alkynylphosphonates

KW - Copper chloride

KW - Cyclization

KW - Cyclobutenylphosphonates

KW - Diethylzirconocene

UR - https://www.scopus.com/pages/publications/58149484914

U2 - 10.1016/j.tetlet.2008.11.108

DO - 10.1016/j.tetlet.2008.11.108

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AN - SCOPUS:58149484914

SN - 0040-4039

VL - 50

SP - 867

EP - 869

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

Direct formation of cyclobutenylphosphonates from 1-alkynylphosphonates and Cp₂ZrCl₂/2EtMgCl/2CuCl

Abstract

Keywords

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