Functionalised acyl ferrocenes: Crystal and molecular structures of 4-aminobenzoylferrocene, 4-hydroxybenzoylferrocene and 1,1′-bis(4-hydroxybenzoyl)ferrocene

Attila C. Bényei; Christopher Glidewell; Philip Lightfoot; Brodyck J.L. Royles; David M. Smith

doi:10.1016/S0022-328X(97)00079-X

Functionalised acyl ferrocenes: Crystal and molecular structures of 4-aminobenzoylferrocene, 4-hydroxybenzoylferrocene and 1,1′-bis(4-hydroxybenzoyl)ferrocene

Attila C. Bényei, Christopher Glidewell^*, Philip Lightfoot, Brodyck J.L. Royles, David M. Smith

^*Corresponding author for this work

School of Chemistry

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Abstract

Improved methods of synthesis are reported for FcCOC₆H₄F-4 1a, FcCOC₆H₄OMe-4 1b and Fcd(COC₆H₄OMe-4)₂ 2b [Fc = (C₅H₅)Fe(C₅H₄); Fcd = (C₅H₄)Fe(C₅H₄)]: demethylation of 1b and 2b, using AlCl₃ in 1,1,2-trichloroethane, yields FcCOC₆H₄OH 1f and Fcd(COC₆H₄OH)₂ 2f respectively. Acylation of ferrocene using 4-phthalimidobenzoyl chloride yields 4-(phthalimidobenzoyl)ferrocene 1c, hydrazinolysis of which yields FcCOC₆H₄NH₂-4 1d. Crystal structures are reported for 1d, 1f and 2f: in 1d and 1f the molecules are linked into spiral chains by means of N-H ⋯ O=C and O-H ⋯ O=C hydrogen bonds respectively; in 2f the O-H ⋯ O=C hydrogen bonds link the centrosymmetric molecules into continuous two-dimensional nets, two independent sets of which are interwoven.

Original language	English
Pages (from-to)	177-186
Number of pages	10
Journal	Journal of Organometallic Chemistry
Volume	539
Issue number	1-2
DOIs	https://doi.org/10.1016/S0022-328X(97)00079-X
Publication status	Published - 1 Jul 1997

Keywords

1,1′-bis(4-hydroxybenzoyl)ferrocene
4-aminobenzoylferrocene
4-hydroxybenzoylferrocene
Acyl ferrocenes
Crystal structure
Molecular structure

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10.1016/S0022-328X(97)00079-X

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@article{1fc38fd82b634d53a48ba4f7afc9c594,

title = "Functionalised acyl ferrocenes: Crystal and molecular structures of 4-aminobenzoylferrocene, 4-hydroxybenzoylferrocene and 1,1′-bis(4-hydroxybenzoyl)ferrocene",

abstract = "Improved methods of synthesis are reported for FcCOC6H4F-4 1a, FcCOC6H4OMe-4 1b and Fcd(COC6H4OMe-4)2 2b [Fc = (C5H5)Fe(C5H4); Fcd = (C5H4)Fe(C5H4)]: demethylation of 1b and 2b, using AlCl3 in 1,1,2-trichloroethane, yields FcCOC6H4OH 1f and Fcd(COC6H4OH)2 2f respectively. Acylation of ferrocene using 4-phthalimidobenzoyl chloride yields 4-(phthalimidobenzoyl)ferrocene 1c, hydrazinolysis of which yields FcCOC6H4NH2-4 1d. Crystal structures are reported for 1d, 1f and 2f: in 1d and 1f the molecules are linked into spiral chains by means of N-H ⋯ O=C and O-H ⋯ O=C hydrogen bonds respectively; in 2f the O-H ⋯ O=C hydrogen bonds link the centrosymmetric molecules into continuous two-dimensional nets, two independent sets of which are interwoven.",

keywords = "1,1′-bis(4-hydroxybenzoyl)ferrocene, 4-aminobenzoylferrocene, 4-hydroxybenzoylferrocene, Acyl ferrocenes, Crystal structure, Molecular structure",

author = "B{\'e}nyei, {Attila C.} and Christopher Glidewell and Philip Lightfoot and Royles, {Brodyck J.L.} and Smith, {David M.}",

year = "1997",

month = jul,

day = "1",

doi = "10.1016/S0022-328X(97)00079-X",

language = "English",

volume = "539",

pages = "177--186",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

number = "1-2",

}

Functionalised acyl ferrocenes: Crystal and molecular structures of 4-aminobenzoylferrocene, 4-hydroxybenzoylferrocene and 1,1′-bis(4-hydroxybenzoyl)ferrocene. / Bényei, Attila C.; Glidewell, Christopher; Lightfoot, Philip et al.
In: Journal of Organometallic Chemistry, Vol. 539, No. 1-2, 01.07.1997, p. 177-186.

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

TY - JOUR

T1 - Functionalised acyl ferrocenes

T2 - Crystal and molecular structures of 4-aminobenzoylferrocene, 4-hydroxybenzoylferrocene and 1,1′-bis(4-hydroxybenzoyl)ferrocene

AU - Bényei, Attila C.

AU - Glidewell, Christopher

AU - Lightfoot, Philip

AU - Royles, Brodyck J.L.

AU - Smith, David M.

PY - 1997/7/1

Y1 - 1997/7/1

N2 - Improved methods of synthesis are reported for FcCOC6H4F-4 1a, FcCOC6H4OMe-4 1b and Fcd(COC6H4OMe-4)2 2b [Fc = (C5H5)Fe(C5H4); Fcd = (C5H4)Fe(C5H4)]: demethylation of 1b and 2b, using AlCl3 in 1,1,2-trichloroethane, yields FcCOC6H4OH 1f and Fcd(COC6H4OH)2 2f respectively. Acylation of ferrocene using 4-phthalimidobenzoyl chloride yields 4-(phthalimidobenzoyl)ferrocene 1c, hydrazinolysis of which yields FcCOC6H4NH2-4 1d. Crystal structures are reported for 1d, 1f and 2f: in 1d and 1f the molecules are linked into spiral chains by means of N-H ⋯ O=C and O-H ⋯ O=C hydrogen bonds respectively; in 2f the O-H ⋯ O=C hydrogen bonds link the centrosymmetric molecules into continuous two-dimensional nets, two independent sets of which are interwoven.

AB - Improved methods of synthesis are reported for FcCOC6H4F-4 1a, FcCOC6H4OMe-4 1b and Fcd(COC6H4OMe-4)2 2b [Fc = (C5H5)Fe(C5H4); Fcd = (C5H4)Fe(C5H4)]: demethylation of 1b and 2b, using AlCl3 in 1,1,2-trichloroethane, yields FcCOC6H4OH 1f and Fcd(COC6H4OH)2 2f respectively. Acylation of ferrocene using 4-phthalimidobenzoyl chloride yields 4-(phthalimidobenzoyl)ferrocene 1c, hydrazinolysis of which yields FcCOC6H4NH2-4 1d. Crystal structures are reported for 1d, 1f and 2f: in 1d and 1f the molecules are linked into spiral chains by means of N-H ⋯ O=C and O-H ⋯ O=C hydrogen bonds respectively; in 2f the O-H ⋯ O=C hydrogen bonds link the centrosymmetric molecules into continuous two-dimensional nets, two independent sets of which are interwoven.

KW - 1,1′-bis(4-hydroxybenzoyl)ferrocene

KW - 4-aminobenzoylferrocene

KW - 4-hydroxybenzoylferrocene

KW - Acyl ferrocenes

KW - Crystal structure

KW - Molecular structure

UR - http://www.scopus.com/inward/record.url?scp=0031185291&partnerID=8YFLogxK

U2 - 10.1016/S0022-328X(97)00079-X

DO - 10.1016/S0022-328X(97)00079-X

M3 - Article

AN - SCOPUS:0031185291

SN - 0022-328X

VL - 539

SP - 177

EP - 186

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 1-2

ER -

Functionalised acyl ferrocenes: Crystal and molecular structures of 4-aminobenzoylferrocene, 4-hydroxybenzoylferrocene and 1,1′-bis(4-hydroxybenzoyl)ferrocene

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