Professional Writing in English
Courseware developed by Kevin Costello
from various sources in the public domain
Intercultural Studies Group
Copyediting
Publishers’ style sheets
Publishing houses often issue their own set of guidelines and instructions on style. This is
known as a style sheet. Here, for example, are some instructions from the style sheet you
can find at the web site of St. Jerome Publishing (http://www.stjerome.co.uk/author.html).
Spelling & Other Conventions
(i) Use -ize rather than -ise generally, except for standard spellings such as advertise and
televise.
(ii) Use British spelling wherever possible, for example humour rather than humor.
(iii) Try to avoid sexist language. Replace he and he or she with they or a repetition of the
noun where possible, otherwise use s/he, his/her and him or her.
(iv) Use endnotes rather than footnotes - if necessary.
(v) Use italics for lexical items and titles of publications and boldface for technical terms.
(vi) Use a single rather than double space after full stops, commas and semicolons.
(vii) Justify your text to the left and do not use the hyphenation facility.
(viii) Send two copies of your manuscript on a PC-compatible disk, one copy in ASCII
format (not preserving line breaks) and one word-processed (preferably using Word 6).
Make sure your printout matches the disk version exactly and provide full details of the
hardware and software used.
(ix) Send a separate list of any characters in your file which are not found on a standard
English keyboard.
The aim is to create consistency among all the texts produced by a given publisher. This is
especially important in journals, magazines and collections of articles, where several
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authors contribute to a single issue or book. Once the contribution arrives, the copyeditor
checks that the instructions have been followed. House style also helps create a distinctive
institutional voice and visual image for a publication.
Exercise 3. Style sheets
Use the style sheet of Analytica Chimica Acta to copyedit the manuscript entitled
Investigative Study in our laboratory of Mixed Thioether-Phosphite and PhosphinePhosphite Ligands Used in Industry for the Copper-Catalyzed Asymmetric 1,4-Addition of
Organometallic Reagents to Cyclohexenone”.
You don’t need to edit the manuscript for style.
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INSTRUCTIONS
TO
AUTHORS
Title and initial layout
The title page should contain only the
manuscript title, the authors' names, their
affiliation, and, for indexing purposes, five
keywords or phrases. In a manuscript by
several authors, the corresponding author's
name should be marked by an asterisk, and
the
footnote
“Author
to
whom
correspondence should be addressed” should
be placed at the bottom of the page.
Abstract
The abstract should not exceed 250 words
and it should condense the essential features
of the review article, with the focus on the
major advances in the field.
Figures
Figures should be referred to as "Fig. (1)",
Fig. (2)" etc. in the text with the Figure
numbers given in bold within round brackets.
Each figure should be accompanied by a
caption, which should describe briefly the
important features displayed in the Figure.
Tables
All tables should be numbered with Arabic
numerals and have brief descriptive headings;
they should be typed on separate pages. The
layout should be given serious thought.
Column headings should be brief, but should
include the units in parentheses, where
relevant. Footnotes to tables are denoted by
superscript a, b, c... The following usage is
recommended: e.g., if molar absorptivities are
listed, the heading should be (104 l mol-1
cm-1) so that a number 2.32 in the column
signifies 23 200.
Acknowledgements
Acknowledgements should be kept to a
minimum. The source of any financial
support received for the work being published
must be indicated in the Acknowledgements
section. (It will be assumed that the absence
of such an acknowledgement is statement by
the authors that no support was received).
Recognition of personal assistance should be
given as a separate paragraph.
References
References should be indicated in the text by
consecutive superior Arabic numbers in
brackets. The full list should be collected and
typed on a separate sheet at the end of the
paper in numerical order. Listed references
should be complete in all details but
excluding article titles in journals. Authors’
initials should precede their names; journal
title abbreviations should conform to the style
of Chemical Abstracts. Examples:
(1) A.B. Smith and C.D. Jones, J. Appl.
Phys, 34, 296-300 (1965).
(2) R.B. Brown Molecular Spectroscopy
(Gordon and Breach, New York,
1970), 3rd ed., 300pp.
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Investigative Study in our laboratory of Mixed Thioether-Phosphite
and Phosphine-Phosphite Ligands Used in Industry for the CopperCatalyzed Asymmetric 1,4-Addition of Organometallic Reagents to
Cyclohexenone.
Montserrat Dominguez, Jordi Pàmies, Gemma Nieto, Amalia Ruiz, Carme Clotet.
Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Pl. Imperial
Tarraco 1, 43005 Tarragona, Spain.
Abstract
A series of thioether-phosphite and phosphine-phosphite ligands have been tested in the
copper-catalyzed asymmetric addition of organometallic regents to 2-cyclohexenone. In
all cases, excellent reaction rates (TOF>1200 h-1) and chemoselectivities for the 1,4product and moderate enantioselectivities have been obtained.
Keywords: Conjugate addition; Copper; Thioether-phosphite; Phosphine-phosphite;
Enantioselective catalysis.
1. Introduction
The 1,4-addition of organometallic reagents to ,-unsaturated carbonyl compounds is
an important process for C-C bond formation in organic synthesis.[ i , ii ] Although
organocuprates and copper catalyzed 1,4-additions of Grignard reagents are most
frequently employed, a number of alternative reagents, based on other metal catalysts
(i.e. Ni and Mn) and on other organometallic reagents (i.e. ZnR2 and AlR3), have been
recently developed.
Several successful methods for enantioselective 1,4-addition have been described.
These were mainly based on chiral auxiliaries or stoichiometric organometallic
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reagents. Only a few were based on highly enantioselective catalytic processes. A
prominent position in the rapid development of the latter field is occupied by the
copper-catalyzed, ligand accelerated, 1,4-addition of organozinc reagents. Thus,
excellent enantioselectivities have been obtained using chiral phosphoroamidites,
phosphites, bidentate P-N ligands and Schiff base ligands. However, further
investigations are required in order to understand how to obtain an efficient
enantiocontrol. In this context, the design of new ligands is still a highly significant
field of research.
Following our interest in using carbohydrates as an available chiral source for ligands
and bearing in mind the idea that two different donor sites can a priori match the
intermediates better and so influence their reactivity and enantioselectivity, we herein
report the use of thioether-phosphite 1 and phosphine-phosphite 2 ligands (Figure 1) in
the enantioselective copper-catalyzed 1,4-addition of organometallic reagents to 2cyclohexenone.
R'
R'
R'
R'
O
RS
O
P
OO
Ph2 P
R'
O
1a
1b
1c
1d
1e
O
R'
O
R = Me; R' = t-Bu
R = i-Pr; R' = t-Bu
R = Ph; R' = t-Bu
R = i-Pr; R' = H
R = Ph, R' = H
O
R'
O
P
OO
Ph2 P
R'
O
O
2a R' = t-Bu
2b R' = H
O
P
OO
O
O
2c (S)ax
2d (R)ax
<<Figure I>>
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Table 1. Asymmetric 1,4-addition of diethylzinc to 2-cyclohexenone.1
O
O
Cu(OTf)
/ L*
2
*
Et
ZnEt 2
TOF2 % Conv3 %-1,44
% ee5
Entry
L*
Solvent
T(ºC)
1
1a
Toluene
0
744
62
98
17 (R)
2
1a
CH2Cl2
0
1116
93
100
18 (R)
3
1a
THF
0
1068
89
97
11 (R)
4
1a
CH2Cl2
25
>1200
100
99
15 (R)
5
1a
CH2Cl2
-20
456
1006
100
13 (R)
6
1a
CH2Cl2
-40
144
357
99
9 (R)
7
1a
CH2Cl2
0
1092
91
99
17 (R)
8
1b
CH2Cl2
0
>1200
100
99
9 (R)
9
1c
CH2Cl2
0
1116
93
100
11 (R)
10
1d
CH2Cl2
0
888
74
100
27 (R)
11
1e
CH2Cl2
0
768
64
99
41 (R)
12
2a
CH2Cl2
0
>1200
100
99
12 (S)
13
2b
CH2Cl2
0
780
65
99
19 (S)
14
2c
CH2Cl2
0
732
61
100
10 (R)
15
2d
CH2Cl2
0
756
63
99
9 (S)
Reaction conditions: Cu(OTf)2 (0.025 mmol), ligand (0.025 mmol),
ZnEt2 (3.5 mmol), substrate (2.5 mmol), solvent (6 mL). 2 TOF in mol
productmol Cu-1h-1 determined after 5 minutes reaction time by GC.
3
% Conversion determined by GC using undecane as internal standard
after 5 minutes. 4 Chemoselectivity in 1,4-product determined by GC
using undecane as internal standard. 5 Enantiomeric excess measured by
GC using Lipodex A column. 6 Conversion determined after 15 minutes. 7
0.05 mmol of ligand used.
1
Acknowledgements
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We thank the Spanish Ministerio de Educación y Cultura and the Generalitat de
Catalunya (CIRIT) for their financial support (PB97-0407-CO5-01). We would also
like to thank Prof. J.P. Watson of the University of Manchester for his invaluable
comments.
References
1
P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford,
1992.
2
K. Tomioka, Y. Nagaoka, in E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.),
Comprehensive Asymmetric Catalysis, Springer: Berlin, 1999; Chapter 31.
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