Synthesis and reactivity of selenium functionalised allylidynes and propargylidynes

Anthony F. Hill; Richard A. Manzano; Jas S. Ward

doi:10.1039/c8dt02370k

Synthesis and reactivity of selenium functionalised allylidynes and propargylidynes

Anthony F. Hill^*, Richard A. Manzano, Jas S. Ward

^*Corresponding author for this work

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

6 Citations (Scopus)

Abstract

The reactions of the trimethylsilylpropargylidyne [W(CCCSiMe₃)(CO)₂(Tp∗)] (1: Tp∗ = hydrotris(dimethylpyrazolyl)borate) towards selenium centred reagents when treated with tetrabutylammonium fluoride (TBAF) were explored in order to prepare alkynylselenolato propargylidynes, e.g., [W(CCCSePh)(CO)₂(Tp∗)]. Treating 1 with TBAF and PhSeSePh resulted in E and Z isomers of the vinylcarbyne (allylidyne) complex [W{CC(SePh)CHSePh}(CO)₂(Tp∗)] in addition to traces of the trisubstituted derivative [W{CC(SePh)C(SePh)₂}(CO)₂(Tp∗)]. Reactions with PhSeCl resulted in the isolation of bimetallic bis-substituted allylidyne complex [(Tp∗)(CO)₂WCC(SePh)C(SePh)CCCW(CO)₂(CO)₂(Tp∗)] as well as the desired selenolatopropargylidyne [W(CCCSePh)(CO)₂(Tp∗)].

Original language	English
Pages (from-to)	14621-14629
Number of pages	9
Journal	Dalton Transactions
Volume	47
Issue number	41
DOIs	https://doi.org/10.1039/c8dt02370k
Publication status	Published - 2018

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title = "Synthesis and reactivity of selenium functionalised allylidynes and propargylidynes",

abstract = "The reactions of the trimethylsilylpropargylidyne [W(CCCSiMe3)(CO)2(Tp∗)] (1: Tp∗ = hydrotris(dimethylpyrazolyl)borate) towards selenium centred reagents when treated with tetrabutylammonium fluoride (TBAF) were explored in order to prepare alkynylselenolato propargylidynes, e.g., [W(CCCSePh)(CO)2(Tp∗)]. Treating 1 with TBAF and PhSeSePh resulted in E and Z isomers of the vinylcarbyne (allylidyne) complex [W{CC(SePh)CHSePh}(CO)2(Tp∗)] in addition to traces of the trisubstituted derivative [W{CC(SePh)C(SePh)2}(CO)2(Tp∗)]. Reactions with PhSeCl resulted in the isolation of bimetallic bis-substituted allylidyne complex [(Tp∗)(CO)2WCC(SePh)C(SePh)CCCW(CO)2(CO)2(Tp∗)] as well as the desired selenolatopropargylidyne [W(CCCSePh)(CO)2(Tp∗)].",

author = "Hill, {Anthony F.} and Manzano, {Richard A.} and Ward, {Jas S.}",

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8dt02370k",

language = "English",

volume = "47",

pages = "14621--14629",

journal = "Dalton Transactions",

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publisher = "Royal Society of Chemistry",

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T1 - Synthesis and reactivity of selenium functionalised allylidynes and propargylidynes

AU - Hill, Anthony F.

AU - Manzano, Richard A.

AU - Ward, Jas S.

PY - 2018

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N2 - The reactions of the trimethylsilylpropargylidyne [W(CCCSiMe3)(CO)2(Tp∗)] (1: Tp∗ = hydrotris(dimethylpyrazolyl)borate) towards selenium centred reagents when treated with tetrabutylammonium fluoride (TBAF) were explored in order to prepare alkynylselenolato propargylidynes, e.g., [W(CCCSePh)(CO)2(Tp∗)]. Treating 1 with TBAF and PhSeSePh resulted in E and Z isomers of the vinylcarbyne (allylidyne) complex [W{CC(SePh)CHSePh}(CO)2(Tp∗)] in addition to traces of the trisubstituted derivative [W{CC(SePh)C(SePh)2}(CO)2(Tp∗)]. Reactions with PhSeCl resulted in the isolation of bimetallic bis-substituted allylidyne complex [(Tp∗)(CO)2WCC(SePh)C(SePh)CCCW(CO)2(CO)2(Tp∗)] as well as the desired selenolatopropargylidyne [W(CCCSePh)(CO)2(Tp∗)].

AB - The reactions of the trimethylsilylpropargylidyne [W(CCCSiMe3)(CO)2(Tp∗)] (1: Tp∗ = hydrotris(dimethylpyrazolyl)borate) towards selenium centred reagents when treated with tetrabutylammonium fluoride (TBAF) were explored in order to prepare alkynylselenolato propargylidynes, e.g., [W(CCCSePh)(CO)2(Tp∗)]. Treating 1 with TBAF and PhSeSePh resulted in E and Z isomers of the vinylcarbyne (allylidyne) complex [W{CC(SePh)CHSePh}(CO)2(Tp∗)] in addition to traces of the trisubstituted derivative [W{CC(SePh)C(SePh)2}(CO)2(Tp∗)]. Reactions with PhSeCl resulted in the isolation of bimetallic bis-substituted allylidyne complex [(Tp∗)(CO)2WCC(SePh)C(SePh)CCCW(CO)2(CO)2(Tp∗)] as well as the desired selenolatopropargylidyne [W(CCCSePh)(CO)2(Tp∗)].

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U2 - 10.1039/c8dt02370k

DO - 10.1039/c8dt02370k

M3 - Article

SN - 1477-9226

VL - 47

SP - 14621

EP - 14629

JO - Dalton Transactions

JF - Dalton Transactions

IS - 41

ER -

Synthesis and reactivity of selenium functionalised allylidynes and propargylidynes

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