Formation of Iridalactones by ch2-o Oxidative Addition of Propiolactone to Iridium(I)

Andrei A. Zlota; Felix Frolow; David Milstein

doi:10.1021/om00118a063

Formation of Iridalactones by ch₂-o Oxidative Addition of Propiolactone to Iridium(I)

Andrei A. Zlota, Felix Frolow, David Milstein

Weizmann Institute of Science, Israel

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

13 Citations (Scopus)

Abstract

Propiolactone undergoes facile oxidative addition to low-valent electron-rich Ir(I) complexes. (C₈H₁₄)Ir(PMe₃)₃Cl (1) yields the structurally characterized iridalactone mer-(CH₂CH₂CO₂)Ir(PMe₃)₃Cl (2) by cleavage of the CH₂-O bond. The reaction is first order in both the lactone and 1. A likely mechanism involves nucleophilic attack by a 16-electron iridium complex on the CH₂-O carbon atom. The structure of 2 has been determined crystallographically [space group P2_l/c; a = 13.184 (5) Å, b = 13.852 (2) Å, c = 12.761 (4) Å; β = 111.20 (5)°; Z = 4; R = 0.033 for 4882 reflections].

Original language	English
Pages (from-to)	1300-1302
Number of pages	3
Journal	Organometallics
Volume	9
Issue number	4
DOIs	https://doi.org/10.1021/om00118a063
Publication status	Published - Jan 1 1990

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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@article{3513c93ff9b64787b1f00c0cf6ff7717,

title = "Formation of Iridalactones by ch2-o Oxidative Addition of Propiolactone to Iridium(I)",

abstract = "Propiolactone undergoes facile oxidative addition to low-valent electron-rich Ir(I) complexes. (C8H14)Ir(PMe3)3Cl (1) yields the structurally characterized iridalactone mer-(CH2CH2CO2)Ir(PMe3)3Cl (2) by cleavage of the CH2-O bond. The reaction is first order in both the lactone and 1. A likely mechanism involves nucleophilic attack by a 16-electron iridium complex on the CH2-O carbon atom. The structure of 2 has been determined crystallographically [space group P2l/c; a = 13.184 (5) {\AA}, b = 13.852 (2) {\AA}, c = 12.761 (4) {\AA}; β = 111.20 (5)°; Z = 4; R = 0.033 for 4882 reflections].",

author = "Zlota, {Andrei A.} and Felix Frolow and David Milstein",

year = "1990",

month = jan,

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doi = "10.1021/om00118a063",

language = "English",

volume = "9",

pages = "1300--1302",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Formation of Iridalactones by ch2-o Oxidative Addition of Propiolactone to Iridium(I)

AU - Zlota, Andrei A.

AU - Frolow, Felix

AU - Milstein, David

PY - 1990/1/1

Y1 - 1990/1/1

N2 - Propiolactone undergoes facile oxidative addition to low-valent electron-rich Ir(I) complexes. (C8H14)Ir(PMe3)3Cl (1) yields the structurally characterized iridalactone mer-(CH2CH2CO2)Ir(PMe3)3Cl (2) by cleavage of the CH2-O bond. The reaction is first order in both the lactone and 1. A likely mechanism involves nucleophilic attack by a 16-electron iridium complex on the CH2-O carbon atom. The structure of 2 has been determined crystallographically [space group P2l/c; a = 13.184 (5) Å, b = 13.852 (2) Å, c = 12.761 (4) Å; β = 111.20 (5)°; Z = 4; R = 0.033 for 4882 reflections].

AB - Propiolactone undergoes facile oxidative addition to low-valent electron-rich Ir(I) complexes. (C8H14)Ir(PMe3)3Cl (1) yields the structurally characterized iridalactone mer-(CH2CH2CO2)Ir(PMe3)3Cl (2) by cleavage of the CH2-O bond. The reaction is first order in both the lactone and 1. A likely mechanism involves nucleophilic attack by a 16-electron iridium complex on the CH2-O carbon atom. The structure of 2 has been determined crystallographically [space group P2l/c; a = 13.184 (5) Å, b = 13.852 (2) Å, c = 12.761 (4) Å; β = 111.20 (5)°; Z = 4; R = 0.033 for 4882 reflections].

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