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SUPPORTING INFORMATION FOR
A Direct Route from White Phosphorus and Fluorous Alkyl and Aryl Iodides to the
Corresponding Trialkyl- and Triarylphosphines
Subrata K. Ghosh,a Christopher C. Cummins,*b and John A. Gladysz*a
aDepartment of Chemistry, Texas A&M University, PO Box 30012, College Station, Texas
77843-3012, USA
E-mail: [email protected]
bDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue,
Cambridge, Massachusetts 02139-4307, USA
E-mail: [email protected]
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.This journal is © the Partner Organisations 2018
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-s2-
P((CH2)2Rf8)31H NMR (CF3C6F11, 500 MHz), internal C6D6 filled capillary
13C{1H} NMR (CF3C6F11, 125 MHz), internal C6D6 filled capillary
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-s3-
31P{1H} NMR (CF3C6F11, 202 MHz), 85% aqueous H3PO4 external standard
-600-550-500-450-400-350-300-250-200-150-100-50050100150200250300350400f1 (ppm)
-25.
20
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-s4-
P((CH2)2Rf10)31H NMR (CF3C6F11, 500 MHz), internal C6D6 filled capillary
13C{1H} NMR (CF3C6F11, 125 MHz), internal C6D6 filled capillary
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-s5-
31P{1H} NMR (CF3C6F11, 202 MHz), 85% aqueous H3PO4 external standard
-260-220-180-140-100-80-60-40-20020406080100120140160180200220240260280f1 (ppm)
-25.
95
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-s6-
P((CH2)3Rf6)31H NMR (CDCl3, 500 MHz)
13C{1H} NMR (CDCl3, 125 MHz)
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-s7-
31P{1H} NMR (CDCl3, 202 MHz), 85% aqueous H3PO4 external standard
-600-550-500-450-400-350-300-250-200-150-100-50050100150200250300350400f1 (ppm)
-33.
16
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-s8-
P((CH2)3Rf8)31H NMR (CF3C6F11, 500 MHz), internal C6D6 filled capillary
13C{1H} NMR (CF3C6F11, 125 MHz), internal C6D6 filled capillary
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-s9-
31P{1H} NMR (CF3C6F11, 202 MHz), 85% aqueous H3PO4 external standard
-600-550-500-450-400-350-300-250-200-150-100-50050100150200250300350f1 (ppm)
-33.
52
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-s10-
P((CH2)4Rf8)31H NMR (CF3C6F11, 500 MHz), internal C6D6 filled capillary
13C{1H} NMR (CF3C6F11, 125 MHz), internal C6D6 filled capillary
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-s11-
31P{1H} NMR (CF3C6F11, 202 MHz), 85% aqueous H3PO4 external standard
-600-550-500-450-400-350-300-250-200-150-100-50050100150200250300350400f1 (ppm)
-32.
07
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-s12-
P(C6H3(3,5-Rf6)2)31H NMR (FC-72, 500 MHz), internal C6D6 filled capillary
31P{1H} NMR (FC-72, 202 MHz), 85% aqueous H3PO4 external standard
-180-160-140-120-100-80-60-40-20020406080100120140160180f1 (ppm)
-5.3
4
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-s13-
P(C6H4(3-Rf6))31H NMR (CDCl3, 500 MHz)
31P{1H} NMR (CDCl3, 202 MHz), 85% aqueous H3PO4 external standard
-180-160-140-120-100-80-60-40-20020406080100120140160180f1 (ppm)
-6.3
4
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-s14-
P(C6H4(4-Rf6))31H NMR (acetone-d6, 500 MHz)
31P{1H} NMR (acetone-d6, 202 MHz), 85% aqueous H3PO4 external standard
-180-160-140-120-100-80-60-40-20020406080100120140160180f1 (ppm)
-6.3
3