Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
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Cite this: DOI: 10.1039/c0xx00000x
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π-Complexes from acyl cyanides and lithium dimethylcuprate(I)
Steven H. Bertz,*a Richard A. Hardin,a Michael D. Murphya and Craig A. Ogle*a
Electronic Supplementary Information
This journal is © The Royal Society of Chemistry [year]
[journal], [year], [vol], 00–00 | 1
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
Pyruvonitrile / Me2CuLi·LiI π-Complex
1
H NMR ( 100 °C)
Pyruvonitrile / Me2CuLi·LiI π-Complex
13
C NMR ( 100 °C)
2
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
Pyruvonitrile / Me2CuLi·LiI π-Complex
HMQC ( 100 °C)
Pyruvonitrile / Me2CuLi·LiI π-Complex
HMBC ( 100 °C)
3
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
Pyruvonitrile / Me2CuLi·LiI π-Complex
HMBC ( 100 °C)
Pyruvonitrile / Me2CuLi·LiI π-Complex
1-D NOE (irradiation offset = 1.40 ppm) ( 100 °C)
4
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
Benzoyl cyanide / Me2CuLi·LiI π-Complex
1
H NMR ( 100 °C)
Benzoyl cyanide / Me2CuLi·LiI π-Complex
13
C NMR ( 100 °C)
5
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
Benzoyl cyanide / Me2CuLi·LiI π-Complex
HMQC ( 100 °C)
Benzoyl cyanide / Me2CuLi·LiI π-Complex
HMBC ( 100 °C)
6
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
Benzoyl cyanide / Me2CuLi·LiI π-Complex
HMBC ( 100 °C)
7
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
Study of the benzoyl cyanide / Me2CuLi·LiI π-complex using isotopic labelling.
References
1. Preparation of CuCN: Reid, J.C.; Weaver, J.C. Cancer Research 1951, 11, 188-194.
2. Preparation of benzoyl cyanide: Oakwood, T.S.; Weisgerber, C.A. Org. Synth. 1944, 24,
14-16.
Note that in the titles below the number of stars (*) refers to the number of labeled atoms.
8
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
***Benzoyl cyanide (Substrate Only)
13
C (carbonyl carbon) ( 100 °C)
9
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
***Benzoyl cyanide (Substrate Only)
13
C (cyano carbon) ( 100 °C)
10
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
***Benzoyl cyanide (Substrate Only)
15
N (cyano nitrogen) ( 100 °C)
11
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
***Benzoyl cyanide / **Me2CuLi·LiI π-Complex
13
C (carbonyl carbon) ( 100 °C)
12
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
***Benzoyl cyanide / **Me2CuLi·LiI π-Complex
13
C (cyano carbon) ( 100 °C)
13
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
***Benzoyl cyanide / **Me2CuLi·LiI π-Complex
15
N (cyano nitrogen) ( 100 °C)
14
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
***Benzoyl cyanide / **Me2CuLi·LiI π-Complex
13
C (CuMe cis to carbonyl C) ( 100 °C)
15
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2013
***Benzoyl cyanide / **Me2CuLi·LiI π-Complex
13
C (CuMe trans to carbonyl C) ( 100 °C)
16