September 2014 Volume 38 Issue 9 Abstracts - Science Reviews ...

This is a compilation of the Abstracts from this issue of the Journal of Chemical Research

September 2014

Volume 38

Issue 9

Abstracts

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Journal of Chemical Research 2014 Volume 38 ISSN 1747-5198

Contents

Issue No. 9 JRPSDC

RESEARCH PAPERS

515

Synthesis of novel indolizine, pyrrolo[1,2‑a] quinoline, and 4,5-dihydrothiophene derivatives via nitrogen ylides and their antimicrobial evaluation Sobhi M. Gomha and Kamal M. Dawood

520

Synthesis, crystal structure, and fungicidal activity of novel 1‑aryl-3-oxypyrazoles containing a Z‑configuration methyl 2-(methoxyimino) acetate moiety Yuanyuan Liu, Yi Li, Nanqing Chen, Xiaohui Xiong, Lu Yu, Chaoxuan Jing, Qiang Zheng, Kang Du and Huiying Jiang

524

One-pot and three-component synthesis of substituted pyrimidines catalysed by boron sulfuric acid under solvent-free conditions Mehdi Soheilizad, Mehdi Adib and Sami Sajjadifar

528

Synthesis, structure, luminescent property and theoretical studies of 4‑chloro-2,6-bis[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]phenol Li-Zhipeng Tang, Feng Tao, Mei-Ling Cheng and Qi Liu

532

A new flavonoid glycoside from the leaves of Eucalyptus citriodora Xiaopeng Zou, Danying Huang, Cuiliu Zhou, Lianmei Li, Kecheng Chen, Ziying Guo, Sanqing Lin, Wenqing Yin and Zhongliu Zhou

535

One-pot site-selective Sonogashira cross-coupling–heteroannulation of the 2‑aryl-6,8-dibromoquinolin-4(1H )-ones: synthesis of novel 6‑H-pyrrolo[3,2,1-ij ]quinolin-6-ones Malose J. Mphahlele and Felix A. Oyeyiola

539

Neofipiperzine D, a new prenylated indole alkaloid metabolite of the fungus Neosartorya fischeri Bing‑Yu Chen, Zhen Wang, You-Min Ying, Lu‑Xi Jiang, Zha-Jun Zhan, Jun‑Lu Wang and Wei Zhang

542

The synthesis of 3,4-disubstituted dihydroquinolin-2(1H)-one under metal-free conditions in aqueous solution Hongyan Wang, Bin Sun, Jun Yang, Jitao Wang, Pu Mao, Liangru Yang and Wenpeng Mai

546

Efficient synthesis of α‑ferrocenyl tertiary alcohols via CeCl3-promoted addition of Grignard reagents to large hindered ketones Haiying Zhao, Wenyao Zhang, Shufeng Chen and Zhanxi Bian

549

Synthesis and antifungal activity of phenacyl azoles Ronald Nelson, Víctor Kesternich, Marcia Pérez-Fehrmann, Fernanda Salazar, Laurence Marcourt, Philippe Christen and Patricio Godoy

553

A facile synthesis of novel indole-based chalcones (E )-1-(2-chloro-1-methyl-1H-indol-3-yl)-3-arylprop-2-en-1-ones Wentao Gao, Shuai Lan, Yang Li, Hong Zhang and Mingqin Chang

558

Synthesis of novel spiro[cyclopropane-indazole] derivatives via magnesium-mediated conjugate addition of bromoform Jinlong Yan, Zhihong Deng and Guoqiang Kuang

562

The role of chlorine interactions in the construction of nickel(II) and cobalt(II) supramolecular metal-organic frameworks based on mixed tetrachloroterephthalate and 2,2′-bipyridine ligands Feng Tian, Jian Gao, Ming-Yang He, Qun Chen and Sheng-Chun Chen

568

Convenient synthesis of bioactive pyranonaphthoquinones (±)9-demethoxyeleutherin and (±)9-demethoxyisoeleutherin Rohan A. Limaye, Augustine R. Joseph, Arun D. Natu and Madhusudan V. Paradkar

571

Synthesis of 2‑aryl-1,1-bis(silyl)alkenes-containing tetrasubstituted imidazoles catalysed by M–Cu/ZSM‑5 (M: Cr, Mn, Co, Ni, V, Zn and Fe) zeolites-supported bimetallic nanostructures Kazem D. Safa, Leila Sarchami, Maryam Allahvirdinesbat, Aynaz Feyzi and Parvaneh Nakhostin Panahi

Click on the titles above to jump straight to the abstract

JOURNAL OF CHEMICAL RESEARCH 2014

VOL. 38

SEPTEMBER, 515–519

RESEARCH PAPER ABSTRACT

Synthesis of novel indolizine, pyrrolo[1,2‑a] quinoline, and 4,5-dihydrothiophene derivatives via nitrogen ylides and their antimicrobial evaluation Sobhi M. Gomha and Kamal M. Dawood Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt Treatment of 2-(2-bromoacetyl)-3H-benzo[f ]chromen-3-one with pyridine, quinoline, and 2‑methylquinoline afforded the corresponding pyridinium, quinolinium and 2‑methylquinolinium bromides. The latter salts underwent [3 + 2] 1,3-dipolar cycloaddition with some electron deficient acetylene and ethylene derivatives to give the corresponding indolizine and pyrrolo[1,2-a]quinoline derivatives. Moreover, 2-(2-bromoacetyl)-3H-benzo[f ]chromen-3-one reacted with arylidene cyanothioacetamides to afford the corresponding 2‑amino-4,5-dihydrothiophene-3-carbonitriles. The synthesised compounds were characterised based on their elemental analysis and spectral data. Antimicrobial activity of some of the synthesised compounds was evaluated. Keywords: indolizine, pyrrolo[1,2-a]quinoline, dihydrothiophene, N‑ylides, cycloaddition

Link to full article: http://ingentaconnect.com/content/stl/jcr/2014/00000038/00000009/art00001


VOL. 38



Synthesis, crystal structure, and fungicidal activity of novel 1‑aryl-3oxypyrazoles containing a Z‑configuration methyl 2-(methoxyimino) acetate moiety Yuanyuan Liua, Yi Lib, Nanqing Chenb, Xiaohui Xiongb, Lu Yua, Chaoxuan Jinga, Qiang Zhenga, Kang Dua and Huiying Jianga a

Department of Chemical and Pharmaceutical Engineering, Southeast University ChengXian College, Nanjing 210088, P.R. China College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, P.R. China

b

Six novel methyl(Z )-2-(4-{[(1-aryl-1H-pyrazol-3-yl)oxy]methyl}phenyl) 2-(methoxyimino)acetate were synthesised by the reaction of 1‑aryl-1H-pyrazol-3-ols with methyl (Z )-2-[4-(bromomethyl)phenyl]-2-(methoxyimino)acetate. The structure of methyl (Z )-2-[4-({[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}methyl)phenyl]-2-(methoxyimino)acetate was also determined by single-crystal X‑ray diffraction analysis. A preliminary in vitro bioassay indicated that compounds 3‑chlorophenyl, 4‑chlorophenyl and 4‑fluoro-3-(trifluoromethyl) derivatives exhibited moderate fungicidal activity against Rhizoctonia solani at a dosage of 10 μg mL–1. Keywords: methyl (Z)-2-(methoxyimino)acetate moiety, 1‑aryl-3-oxypyrazoles, synthesis, crystal structure, fungicidal activity, structure–activity relationships

H3CO N Br

O HO

N

OCH3

N X

K2CO3

H3CO N O

O OCH3

Link to full article: 1a-1f http://ingentaconnect.com/content/stl/jcr/2014/00000038/00000009/art00002

N

N X


VOL. 38



One-pot and three-component synthesis of substituted pyrimidines catalysed by boron sulfuric acid under solvent-free conditions Mehdi Soheilizada, Mehdi Adiba and Sami Sajjadifarb a

School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran Department of Chemistry, Payame Noor University, PO Box 19395-4697 Tehran, Iran

b

An efficient, simple and one-pot synthesis of pyrimidine derivatives by a three-component reaction of ketones, triethyl orthoformate, and ammonium acetate in the presence of boron sulfuric acid as a reusable and efficient catalyst under solventfree conditions is reported. The reusability of catalyst, simplicity of the starting materials, short reaction time, one-pot, and good yields of products are the main advantages. Keywords: boron sulfuric acid, multi-component reactions, pyrimidine, solvent-free, triethyl orthoformate O Ph

OEt CH3

+

EtO

+

OEt

N

Acid catalyst

NH4OAc

solvent-free 100°C

Ph

N



VOL. 38



Synthesis, structure, luminescent property and theoretical studies of 4‑chloro-2,6-bis[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]phenol Li-Zhipeng Tang, Feng Tao, Mei-Ling Cheng and Qi Liu School of Petrochemical Engineering and Key Laboratory of Fine Petrochemical Technology, Changzhou University, Changzhou 213164, P.R. China 4-Chloro-2,6-bis[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]phenol has been synthesised and characterised, including by singlecrystal X‑ray diffraction. The benzene ring system is planar and makes dihedral angles of 88.90°(0.14) and 59.84°(0.11) with two pyrazole rings, respectively, and the two pyrazole rings are arranged trans to each other with the dihedral angles 87.22°(0.15). The luminescent property of the title compound was investigated. The molecular structure of the title compound has been optimised by density functional theory with B3LYP/6-31G (d, p) level, the optimised geometer parameters and vibrational frequencies are consistent with the experiment data. Keywords: synthesis, crystal structure, density functional theory calculation, luminescent property

Cl N

N

N

N OH



VOL. 38



A new flavonoid glycoside from the leaves of Eucalyptus citriodora Xiaopeng Zoua, Danying Huanga, Cuiliu Zhoua, Lianmei Lia, Kecheng Chena, Ziying Guoa, Sanqing Lina, Wenqing Yinb and Zhongliu Zhoua School of Chemistry and Chemical Engineering, Lingnan Normal University, 29 Cunjin Road, Zhanjiang, 524048, P.R. China Ministry of Education Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resource, Guangxi Normal University, 15 Yucai Road, Guilin, 541004, P.R. China a

b

Citrioside A, a new flavonoid glycoside, has been isolated from the n‑butanol soluble fraction of Eucalyptus citriodora, along with five flavonoid glycosides, reported for the first time from Eucalyptus citriodora. Their structures were elucidated on the basis of spectroscopic methods and from literature values. Keywords: Eucalyptus citriodora; citrioside A; flavonoid glycoside OCH3 OH HO OH

HO HO

O

O O

OH

O

O OH HO HO O HO

O O

OH Link to full article: http://ingentaconnect.com/content/stl/jcr/2014/00000038/00000009/art00005


VOL. 38



One-pot site-selective Sonogashira cross-coupling–heteroannulation of the 2‑aryl-6,8-dibromoquinolin-4(1H)-ones: synthesis of novel 6‑H-pyrrolo[3,2,1-ij ]quinolin-6-ones Malose J. Mphahlele and Felix A. Oyeyiola Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, PO Box 392, Pretoria 0003, South Africa The 2‑aryl-6,8-dibromoquinolin-4(1H)-ones were subjected to site-selective Sonogashira cross-coupling with terminal acetylenes as models for Csp2–Csp bond formation in the presence of Pd/C–PPh3 and CuI as catalysts and K 2CO3 as a base in dioxane to afford the 2‑substituted 4‑aryl-8-bromo-4H-pyrrolo[3,2,1-ij ]quinolin-6-ones. These were, in turn, subjected to Suzuki–Miyaura cross-coupling with 4‑fluorophenylboronic acid as coupling partner to afford the 2‑substituted 4,8-diaryl-4Hpyrrolo[3,2,1-ij ]quinolin-6-ones. Keywords:  2‑aryl-6,8-dibromoquinolin-4(1H)-ones, Sonogashira cross-coupling; 2,4-diaryl-8-bromo-4H-pyrrolo[3,2,1-ij] quinolin-6-ones, Suzuki–Miyaura cross-coupling, 2,4,8-triaryl-6H-pyrrolo[3,2,1-ij]quinolin-6-ones

O

F

Br

O

(i) N C6H5

C6H4R

N

C6H4R

C6H5



VOL. 38



Neofipiperzine D, a new prenylated indole alkaloid metabolite of the fungus Neosartorya fischeri Bing‑Yu Chena, Zhen Wanga, You-Min Yingd, Lu‑Xi Jianga, Zha-Jun Zhand, Jun‑Lu Wangc and Wei Zhanga,b Institute of Molecular Medicine, Department of Blood Transfusion, Zhejiang Provincial People’s Hospital, Hangzhou, 310014, P.R. China Department of Gastrointestinal Surgery, Zhejiang Provincial People’s Hospital, Hangzhou, 310014, P.R. China c Department of Anesthesia, The First Affiliated Hospital of Wenzhou Medical University, Wenzhou, 325000, P.R. China d College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, P.R. China a

b

A new prenylated indole alkaloid, neofipiperzine D, was isolated from the cultures of Neosartorya fischeri, together with three known metabolites fumitremorgin C, ergosterol, and ergosterol peroxide. The structure of the new compound was established by detailed analysis of its spectroscopic data, especially 1D, 2D NMR and HR‑ESI‑MS data. In an in vitro assay, neofipiperzine D did not exhibit any significant cytotoxicity against MCF‑7, H1299, HUVEC, and MDA-MB-231 cell lines at a concentration of 20 µM. Keywords: Neosartorya fischeri, diketopiperazine, alkaloid, fumitremorgin C

O

O N 1H-1H

N

N

O

COSY

HMBC (H

O

C)



VOL. 38



The synthesis of 3,4-disubstituted dihydroquinolin-2(1H)-one under metalfree conditions in aqueous solution Hongyan Wang, Bin Sun, Jun Yang, Jitao Wang, Pu Mao, Liangru Yang and Wenpeng Mai Chemistry and Chemical Engineering School, Henan University of Technology, Henan Province, Zhengzhou 450001, P.R. China A novel route toward 3,4-disubstituted dihydroquinolin-2(1H )-ones via radical process has been developed in aqueous solution without metals. This method offers a new and simple route for the synthesis of skeleton of dihydroquinolin-2(1H )-one in one step. Keywords: dihydroquinolin-2(1H)-one, metal-free conditions, aqueous solution

R3 H R1

R2 N

O O

O

R3 +

K2S2O8, 2.0eq CH3CN/H2O

H

O

O

R1

metal-f ree C-H Functionalization 6-endo-trig cyclization


N R2

O


VOL. 38



Efficient synthesis of α‑ferrocenyl tertiary alcohols via CeCl3-promoted addition of Grignard reagents to large hindered ketones Haiying Zhao, Wenyao Zhang, Shufeng Chen and Zhanxi Bian College of Chemistry and Chemical Engineering, Inner Mongolia University, Huhhot 010021, P.R. China The addition of Grignard reagents to highly hindered acylferrocenes in the presence of anhydrous CeCl3 at room temperature provided the corresponding α‑ferrocenyl tertiary alcohols FcC(OH)R1R2 (R1 = Ph or Fc, R2 = Me, Et, i Pr, n Bu, Ph; Fc = C5H4FeC5H5) in moderate to high yields. Optimum conditions and factors affecting the reaction were investigated. Keywords: α-ferrocenyl ketone, Grignard reaction, anhydrous cerium chloride, α‑ferrocenyl tertiary alcohol



VOL. 38



Synthesis and antifungal activity of phenacyl azoles Ronald Nelsona, Víctor Kesternicha, Marcia Pérez-Fehrmanna, Fernanda Salazara, Laurence Marcourtb, Philippe Christenb and Patricio Godoyc Departamento de Química, Facultad de Ciencias, Universidad Católica del Norte, Antofagasta, Chile School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Quai Ernest-Ansermet 30, CH‑1211 Geneva 4, Switzerland c Instituto de Microbiología Clínica, Facultad de Medicina, Universidad Austral de Chile, Valdivia, Chile a

b

A new N-(4-methoxyphenacyl)imidazole and three new substituted N-(phenacyl)triazoles were prepared by reaction of the heterocycle with a phenacyl halide. The former ketone and one example of the latter were reduced to the corresponding alcohols. All six compounds were screened in vitro for antifungal activity against two pathogenic fungal strains, Candida albicans (fluconazole-resistant) and Aspergillus fumigatus. The results revealed that most of the compounds showed activity against both strains at 100 µg mL–1 and 80 µg mL–1, some comparable with control compound fluconazole. The alcohols were less active than the corresponding ketones. Keywords: N-(4-methoxyphenacyl)imidazole, N-(phenacyl)-1,2,4-triazoles, fluconazole, antifungal activity



VOL. 38



A facile synthesis of novel indole-based chalcones (E)-1-(2-chloro-1-methyl-1H -indol-3-yl)-3-arylprop-2-en-1-ones Wentao Gaoa, Shuai Lana, Yang Lia, Hong Zhangb and Mingqin Changb a

Institute of Superfine Chemicals, Bohai University, Jinzhou 121 000, P.R. China College of Chemistry & Chemical Engineering, Bohai University, Jinzhou 121000, P.R. China

b

A facile and general synthesis of 23 novel indole-based chalcones, (E )-1-(2-chloro-1-methyl-1H-indol-3-yl)-3-arylprop-2-en1-ones, has been achieved in good yields of 71–89% by the Claisen–Schmidt condensation reaction of 3‑acetyl-2-chloro-Nmethylindole with variously substituted araldehydes using 1,4-dioxane as solvent in the presence of 5% aq. KOH. A similar reaction using furan‑2- or thiophene-2-carbaldehyde gave analogous products in good yield, but an unexpected aldol reaction occurred with 2‑nitrobenzaldehyde and the stable aldol product was isolated as the major product in a good yield of 73%. Keywords: indole-based chalcone, Claisen–Schmidt condensation reaction, aromatic aldehyde, aldol reaction, 1,4-dioxane

O CHO R Cl +

O

5% KOH, 1,4-dioxane stir, r. t.

N

R N

Cl



VOL. 38



Synthesis of novel spiro[cyclopropane-indazole] derivatives via magnesium-mediated conjugate addition of bromoform Jinlong Yana, Zhihong Dengb and Guoqiang Kuangb Department of Biology and Chemical Engineering, Jiaozuo Teachers College, Jiaozuo, Henan 454001, P.R. China Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/ QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201, P.R. China a

b

A novel series of 2,2-dibromo-3-aryl-1′-phenyl-6′,7′-dihydrospiro[cyclopropane-1,5′-indazol]-4′(1′H)-ones derivatives were prepared in moderate to good yields by conjugate addition of bromoform to (E )-5-arylmethylene-1-phenyl-6,7-dihydro-1Hindazol-4(5H)-ones in the presence of magnesium under N2. The structures of all the products were characterised by 1H NMR, 13 C NMR, IR spectroscopy, elemental analysis and mass spectrometry. Keywords: cyclopropane, indazole, spiroheterocyclic

O

O

Cl O N H

R


O

O


VOL. 38



The role of chlorine interactions in the construction of nickel(II) and cobalt(II) supramolecular metal-organic frameworks based on mixed tetrachloroterephthalate and 2,2′-bipyridine ligands Feng Tiana, Jian Gaob, Ming-Yang Hea, Qun Chena,b and Sheng-Chun Chena,b a

Key Laboratory of Fine Petro-chemical Technology, Changzhou University, Changzhou 213164, P.R. China School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094, P.R. China

b

Reactions of the rigid ligand 2,3,5,6-tetrachloro-1,4-benzenedicarboxylic acid (H2BDC–Cl4) with nickel(II) and cobalt(II) metal salts in the presence of 2,2′-bipyridine in DMF/MeOH afforded [M(BDC–Cl4)(2,2′-bpy)(MeOH)2]n (M = Ni or Co). The Ni complex has a one-dimensional (1‑D) linear structure that is further extended into a three-dimensional (3‑D) supramolecular framework by inter-chain C–H···Cl hydrogen bonds, whereas the Co compound shows a 1‑D zigzag structure, which is further assembled into a 3‑D supramolecular architecture through intermolecular C–H···Cl and Cl···Cl interactions. These results reveal that weak chlorine interactions play an important role in governing these supramolecular structures. Thermal and fluorescence properties have also been investigated. Keywords: Ni, Co, coordination polymers, tetrachloroterephthalic acid, chlorine interaction



VOL. 38



Convenient synthesis of bioactive pyranonaphthoquinones (±)9-demethoxyeleutherin and (±)9-demethoxyisoeleutherin Rohan A. Limaye, Augustine R. Joseph, Arun D. Natu and Madhusudan V. Paradkar Postgraduate and Research Centre, Department of Chemistry, MES Abasaheb Garware College, Karve Road, Pune–411004, India A convenient synthesis of (±)9-demethoxyeleutherin and (±)9-demethoxyisoeleutherin, the analogues of naturally occurring pyranonaphthoquinone antibiotics eleutherin and isoeleutherin, is described. The synthesis was achieved from 4‑methoxy-1napthol in four simple steps including Claisen rearrangement and oxymercuration–demercuration reactions. Keywords: pyranonaphthoquinones, Claisen rearrangement, 9‑demethoxyeleutherin, 9‑demethoxyisoeleutherin, 4‑methoxy-1napthol, eleutherin and isoeleutherin O

O O

O

O

O

(±) 9-Demethoxyeleutherin

(±) 9-Demethoxyisoeleutherin



VOL. 38



Synthesis of 2‑aryl-1,1-bis(silyl)alkenes-containing tetrasubstituted imidazoles catalysed by M–Cu/ZSM‑5 (M: Cr, Mn, Co, Ni, V, Zn and Fe) zeolites-supported bimetallic nanostructures Kazem D. Safaa, Leila Sarchamia, Maryam Allahvirdinesbata, Aynaz Feyzia and Parvaneh Nakhostin Panahib a

Organosilicon Research Laboratory, Faculty of Chemistry, University of Tabriz, 5166616471, Tabriz, Iran Department of Chemistry, Faculty of Science, University of Zanjan, Iran

b

The one-pot synthesis of tetrasubstituted imidazoles by using a series of M–Cu/ZSM‑5 (M: Cr, Mn, Co, Ni, V, Zn and Fe) zeolitessupported bimetallic catalysts was studied. Fe–Cu/ZSM‑5 bimetallic oxide catalyst had the highest activity in improving the efficiency of the heterogeneous cyclo-condensation reaction. Some imidazole derivatives terminated by vinylbis(silanes) have been synthesised using (Me3Si)3CLi through the Peterson olefination reaction. Keywords: imidazole derivatives, bimetallic zeolites-supported nanostructures, Fe–Cu/ZSM‑5, 2‑aryl-1,1-bis(silyl)alkenes, Peterson olefination reaction

R2 R2

O Fe-Cu/ZSM-5

H2N O

O

or OH

+

N

H O NH4OAc

N

Solvent-free 70 oC R1

R1


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