Medium size macrocycles incorporating combinations of coordinated-1,3-diyne units, oxygen donors and group 14 elements

Robert C.J. Atkinson; Louisa J. Hope-Weeks; Martin J. Mays; Gregory A. Solan

doi:10.1016/j.jorganchem.2007.01.026

Medium size macrocycles incorporating combinations of coordinated-1,3-diyne units, oxygen donors and group 14 elements

Robert C.J. Atkinson, Louisa J. Hope-Weeks, Martin J. Mays, Gregory A. Solan

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

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Abstract

Two approaches have been employed to prepare medium size macrocycles incorporating combinations of coordinated-1,3-diyne units, oxygen donors and group 14 elements. In the first approach, the acid-catalysed reaction of [{Co₂(CO)₆(μ-η²-HOCH₂C{triple bond, long}C{single bond})}₂] (1a) with either C₆H₅OH, C₆H₄-1,4-(OH)₂ or C₆H₄-1,2-(OH)₂ was found to form in good to moderate yield the nine-membered [{Co₂(CO)₆}₂{cyclo-μ-η²:μ-η²-CH₂C₂C₂CH₂OC₆H₄}₂] (2) and the eight-membered macrocycles, [{Co₂(CO)₆}₂{cyclo-μ-η²:μ-η²-CH₂C₂C₂CH₂-2,3-C₆H₂-1,4-(OH)₂}] (3) and [{Co₂(CO)₆}₂{cyclo-μ-η²:μ-η²-CH₂C₂C₂CH₂-3,4-C₆H₂-1,2-(OH)₂}] (4), respectively. In contrast, treatment of the bis-lithiated derivative of 1a with Cl₂SiR¹R² affords the silicon-containing nine-membered macrocycles [{Co₂(CO)₆}₂{cyclo-μ-η²:μ-η²-OCH₂C₂C₂CH₂OSiR¹R²}] (5a R¹ = R² = Me; 5b R¹ = R² = Ph; 5c R¹ = Me, R² = Ph). Similarly, the germanium analogue of 5b, [{Co₂(CO)₆}₂{cyclo-μ-η²:μ-η²-OCH₂C₂C₂CH₂OGePh₂}] (6) can be prepared from Cl₂GePh₂. Single crystal X-ray diffraction studies have been reported on 2, 3, 5a, 5b and 6.

Original language	English
Pages (from-to)	2076-2085
Number of pages	10
Journal	Journal of Organometallic Chemistry
Volume	692
Issue number	10
DOIs	https://doi.org/10.1016/j.jorganchem.2007.01.026
State	Published - Apr 15 2007

Keywords

Cobalt
Coordinated 1,3-diyne
Group 14
Macrocycle
Oxygen donor

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@article{d73a53d3446e404f8214780ca186ad21,

title = "Medium size macrocycles incorporating combinations of coordinated-1,3-diyne units, oxygen donors and group 14 elements",

abstract = "Two approaches have been employed to prepare medium size macrocycles incorporating combinations of coordinated-1,3-diyne units, oxygen donors and group 14 elements. In the first approach, the acid-catalysed reaction of [{Co2(CO)6(μ-η2-HOCH2C{triple bond, long}C{single bond})}2] (1a) with either C6H5OH, C6H4-1,4-(OH)2 or C6H4-1,2-(OH)2 was found to form in good to moderate yield the nine-membered [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-CH2C2C2CH2OC6H4}2] (2) and the eight-membered macrocycles, [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-CH2C2C2CH2-2,3-C6H2-1,4-(OH)2}] (3) and [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-CH2C2C2CH2-3,4-C6H2-1,2-(OH)2}] (4), respectively. In contrast, treatment of the bis-lithiated derivative of 1a with Cl2SiR1R2 affords the silicon-containing nine-membered macrocycles [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-OCH2C2C2CH2OSiR1R2}] (5a R1 = R2 = Me; 5b R1 = R2 = Ph; 5c R1 = Me, R2 = Ph). Similarly, the germanium analogue of 5b, [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-OCH2C2C2CH2OGePh2}] (6) can be prepared from Cl2GePh2. Single crystal X-ray diffraction studies have been reported on 2, 3, 5a, 5b and 6.",

keywords = "Cobalt, Coordinated 1,3-diyne, Group 14, Macrocycle, Oxygen donor",

author = "Atkinson, {Robert C.J.} and Hope-Weeks, {Louisa J.} and Mays, {Martin J.} and Solan, {Gregory A.}",

year = "2007",

month = apr,

day = "15",

doi = "10.1016/j.jorganchem.2007.01.026",

language = "English",

volume = "692",

pages = "2076--2085",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

number = "10",

}

TY - JOUR

T1 - Medium size macrocycles incorporating combinations of coordinated-1,3-diyne units, oxygen donors and group 14 elements

AU - Atkinson, Robert C.J.

AU - Hope-Weeks, Louisa J.

AU - Mays, Martin J.

AU - Solan, Gregory A.

PY - 2007/4/15

Y1 - 2007/4/15

N2 - Two approaches have been employed to prepare medium size macrocycles incorporating combinations of coordinated-1,3-diyne units, oxygen donors and group 14 elements. In the first approach, the acid-catalysed reaction of [{Co2(CO)6(μ-η2-HOCH2C{triple bond, long}C{single bond})}2] (1a) with either C6H5OH, C6H4-1,4-(OH)2 or C6H4-1,2-(OH)2 was found to form in good to moderate yield the nine-membered [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-CH2C2C2CH2OC6H4}2] (2) and the eight-membered macrocycles, [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-CH2C2C2CH2-2,3-C6H2-1,4-(OH)2}] (3) and [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-CH2C2C2CH2-3,4-C6H2-1,2-(OH)2}] (4), respectively. In contrast, treatment of the bis-lithiated derivative of 1a with Cl2SiR1R2 affords the silicon-containing nine-membered macrocycles [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-OCH2C2C2CH2OSiR1R2}] (5a R1 = R2 = Me; 5b R1 = R2 = Ph; 5c R1 = Me, R2 = Ph). Similarly, the germanium analogue of 5b, [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-OCH2C2C2CH2OGePh2}] (6) can be prepared from Cl2GePh2. Single crystal X-ray diffraction studies have been reported on 2, 3, 5a, 5b and 6.

AB - Two approaches have been employed to prepare medium size macrocycles incorporating combinations of coordinated-1,3-diyne units, oxygen donors and group 14 elements. In the first approach, the acid-catalysed reaction of [{Co2(CO)6(μ-η2-HOCH2C{triple bond, long}C{single bond})}2] (1a) with either C6H5OH, C6H4-1,4-(OH)2 or C6H4-1,2-(OH)2 was found to form in good to moderate yield the nine-membered [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-CH2C2C2CH2OC6H4}2] (2) and the eight-membered macrocycles, [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-CH2C2C2CH2-2,3-C6H2-1,4-(OH)2}] (3) and [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-CH2C2C2CH2-3,4-C6H2-1,2-(OH)2}] (4), respectively. In contrast, treatment of the bis-lithiated derivative of 1a with Cl2SiR1R2 affords the silicon-containing nine-membered macrocycles [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-OCH2C2C2CH2OSiR1R2}] (5a R1 = R2 = Me; 5b R1 = R2 = Ph; 5c R1 = Me, R2 = Ph). Similarly, the germanium analogue of 5b, [{Co2(CO)6}2{cyclo-μ-η2:μ-η2-OCH2C2C2CH2OGePh2}] (6) can be prepared from Cl2GePh2. Single crystal X-ray diffraction studies have been reported on 2, 3, 5a, 5b and 6.

KW - Cobalt

KW - Coordinated 1,3-diyne

KW - Group 14

KW - Macrocycle

KW - Oxygen donor

UR - http://www.scopus.com/inward/record.url?scp=33947592845&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2007.01.026

DO - 10.1016/j.jorganchem.2007.01.026

M3 - Article

AN - SCOPUS:33947592845

VL - 692

SP - 2076

EP - 2085

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 10

ER -