XII
Table of Contents
6.1.9 Natural Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 270
6.1.10 Reference Compounds . . . . . . . . . . . . . . . . . . . . . . . . . 274
6.1.11 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 275
6.2 19 F NMR Spectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 277
6.2.1 19 F Chemical Shifts of Perfluoroalkanes . . . . . . . . . . . . . . . 277
6.2.2 Estimation of 19 F Chemical Shifts of Substituted
Fluoroethylenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 281
6.2.3 Coupling Constants in Fluorinated Alkanes and Alkenes . . . . 282
6.2.4 19 F Chemical Shifts of Allenes and Alkynes . . . . . . . . . . . . 283
6.2.5 19 F Chemical Shifts and Coupling Constants of Fluorinated
Alicyclics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 284
6.2.6 19 F Chemical Shifts and Coupling Constants of Aromatics
and Heteroaromatics . . . . . . . . . . . . . . . . . . . . . . . . . . . 285
6.2.7 19 F Chemical Shifts of Alcohols and Ethers . . . . . . . . . . . . 288
6.2.8 19 F Chemical Shifts of Fluorinated Amine, Imine, and
Hydroxyl amine Derivatives . . . . . . . . . . . . . . . . . . . . . . . 289
6.2.9 19 F Chemical Shifts of Sulfur Compounds . . . . . . . . . . . . . 290
6.2.10 19 F Chemical Shifts of Carbonyl and Thiocarbonyl
Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 291
6.2.11 19 F Chemical Shifts of Fluorinated Boron, Phosphorus,
and Silicon Compounds . . . . . . . . . . . . . . . . . . . . . . . . 292
6.2.12 19 F Chemical Shifts of Natural Product Analogues . . . . . . . 293
6.2.13 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 294
6.3 29 Si NMR Spectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 295
6.3.1 Silicon-Carbon Compounds . . . . . . . . . . . . . . . . . . . . . . . 295
6.3.2 Silicon-Halogen Compounds . . . . . . . . . . . . . . . . . . . . . . 296
6.3.3 Silicon-Oxygen, Nitrogen, and Sulfur Compounds . . . . . . . . 297
6.3.4 Organic Di- and Oligosilicon Compounds. . . . . . . . . . . . . . 297
6.3.5 Silicon-Organic Phosphorus Compounds . . . . . . . . . . . . . . 298
6.3.6 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 298
6.4 31 P NMR Spectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 299
6.4.1 31 P Chemical Shifts of Tricoordinated Phosphorus, PR 1 R 2 R 3 . 299
6.4.2 31 P Chemical Shifts of Tetracoordinated Phosphonium
Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 300
6.4.3 31 P Chemical Shifts of Compounds with a P=C or P=N Bond . 301
6.4.4 31 P Chemical Shifts of Tetracoordinated P(=O) and P(=S)
Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 302
6.4.5 31 P Chemical Shifts of Penta- and Hexacoordinated
Phosphorus Compounds . . . . . . . . . . . . . . . . . . . . . . . . . 304
6.4.6 31 P Chemical Shifts of Natural Phosphorus Compounds . . . . 305
Table of Contents
6.1.9 Natural Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 270
6.1.10 Reference Compounds . . . . . . . . . . . . . . . . . . . . . . . . . 274
6.1.11 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 275
6.2 19 F NMR Spectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 277
6.2.1 19 F Chemical Shifts of Perfluoroalkanes . . . . . . . . . . . . . . . 277
6.2.2 Estimation of 19 F Chemical Shifts of Substituted
Fluoroethylenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 281
6.2.3 Coupling Constants in Fluorinated Alkanes and Alkenes . . . . 282
6.2.4 19 F Chemical Shifts of Allenes and Alkynes . . . . . . . . . . . . 283
6.2.5 19 F Chemical Shifts and Coupling Constants of Fluorinated
Alicyclics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 284
6.2.6 19 F Chemical Shifts and Coupling Constants of Aromatics
and Heteroaromatics . . . . . . . . . . . . . . . . . . . . . . . . . . . 285
6.2.7 19 F Chemical Shifts of Alcohols and Ethers . . . . . . . . . . . . 288
6.2.8 19 F Chemical Shifts of Fluorinated Amine, Imine, and
Hydroxyl amine Derivatives . . . . . . . . . . . . . . . . . . . . . . . 289
6.2.9 19 F Chemical Shifts of Sulfur Compounds . . . . . . . . . . . . . 290
6.2.10 19 F Chemical Shifts of Carbonyl and Thiocarbonyl
Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 291
6.2.11 19 F Chemical Shifts of Fluorinated Boron, Phosphorus,
and Silicon Compounds . . . . . . . . . . . . . . . . . . . . . . . . 292
6.2.12 19 F Chemical Shifts of Natural Product Analogues . . . . . . . 293
6.2.13 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 294
6.3 29 Si NMR Spectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 295
6.3.1 Silicon-Carbon Compounds . . . . . . . . . . . . . . . . . . . . . . . 295
6.3.2 Silicon-Halogen Compounds . . . . . . . . . . . . . . . . . . . . . . 296
6.3.3 Silicon-Oxygen, Nitrogen, and Sulfur Compounds . . . . . . . . 297
6.3.4 Organic Di- and Oligosilicon Compounds. . . . . . . . . . . . . . 297
6.3.5 Silicon-Organic Phosphorus Compounds . . . . . . . . . . . . . . 298
6.3.6 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 298
6.4 31 P NMR Spectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 299
6.4.1 31 P Chemical Shifts of Tricoordinated Phosphorus, PR 1 R 2 R 3 . 299
6.4.2 31 P Chemical Shifts of Tetracoordinated Phosphonium
Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 300
6.4.3 31 P Chemical Shifts of Compounds with a P=C or P=N Bond . 301
6.4.4 31 P Chemical Shifts of Tetracoordinated P(=O) and P(=S)
Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 302
6.4.5 31 P Chemical Shifts of Penta- and Hexacoordinated
Phosphorus Compounds . . . . . . . . . . . . . . . . . . . . . . . . . 304
6.4.6 31 P Chemical Shifts of Natural Phosphorus Compounds . . . . 305