Supporting information for J. Am. Chem. Soc., 1973, 95(10), , DOI: /ja00791a018
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1 Supporting information for J. Am. Chem. Soc., 973, 95(0), , DOI: 0.0/ja0079a08 Terms & Conditions Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machinereadable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at Copyright 973 American Chemical Society
2 Nmr Spectra Measured in Acetoned6 379M b Chemical Compound Shift,a PPM (J. Hz) Area Chemical Shift,b Assignment Ambient (Area) Low T(J,Hz) B Decoup (J, Hz) Ic,7 (3) 6.55() Cation 5.60() Cage CH + 6.3(7) (6) (36) 3d II C 6.4 (60) 6.58 () 6.55 Cation (35) 7.9() 6.79 (I) 6.74(7)' HCH 7.7(7)' HCH CH 7.48() 7.40 Cage +. (30)(30) 3.6(3) + 3.3(45). 0.8(45) 8.(50) (30)
3 *7» MU 0.6 L (0 7.7 (9) Cage CH Methyl ,8 (58) 8.8(36).9(73) 9.3(6) 3.(45) 0.6(37) 7.5(45) 5.6(45) 0.8(3Q) S.ö (66).6(30) 0.9 (39) 6.45( () 7.47( (3).6(0) 6.45(0 8.3 (3) 8.67 (3) 6.44 (6) g (6) f 6.59 j 6.50(6) g (6) f S.I 6.45(6) g.h S.h (6) (6) f (6) f HCH Cation Cage CH Methyl Cation CH3CH Methyl Methyl
4 I 3TS IM 7. (64) 9.3(3) >0. (43) > 9. (53) >.7(30) > 8.3(45).95(5) 5.63(0 6.65() 7.4 (0.9 d.k Phenyl C6H5CH Cation Cage CH (MS). (MS) > 5.8(45) >.4 (60) > 8. (45) *.90 (0) 5.9(0 6.7 () Phenyl C6H5CH Cation.3 (46) 9.() > 0.(30) > 8.9 (45) >.6(30) >0. (MS) 3.3 (4) 5.66(0 6.6 () 7.(0 EpC6H«FC6H4CH Cation Cage CH
5 97 IM IX c 7.4 (37) 3. (4) d 9.(4) 5.68() 0.(45) 6.68() 49.3 (53) 6.99(0 3. (45) 48.7 (37) mfc6h4 FC6H4CH Cation Cage CH a b c d Relative to external BF3 O(CH5) Relative to internal tetramethyls???lane Tetramethylammonium salt Multiplet e Meaaured at 50o f Doublet g h Quartet fetraphenylarsonium salt i Measured at 70o J Meaaured at 60o k Meaaured at 80
6 Infrared Spectra (cm )a 379 M6 Ib II b 950V, 5, H80vs, 0m, 370, I300w, 80». U90, 70m, IMOm, 090m, 060s. 040, MXBm, 985ß, 950, 984w, 970w, 800», 76», 734w, 7w, 70> 900vs, S0v», ß. 40m. 380m, D90w, 60w. 0m, 090m, 055m, KXKm, 990m, 95vs, 905», 875», 848», 75bn, 730m 305». 880vs, 560ve, 400, 90m, 60», 470, 460ve. MOOm. 370m. 45m. 40m, 80s, 70, 30m, UM. 080m,»45m. 05m, lobm, 988, 980, 853, 740m, 78, 78». 7», 695» IV b 90v, 50V8, 480, 460s, 430m, 380, 340m, 90», 60», 40». 090m, 060m. 00s, MOO. 95, 90», 880». 87», 838m. 830m, 78m, 69» V b 304Cva, 560vs, 75», HSO. Mm. 370m, 350m. 35», 300». 70», X)w, 60», 045m, M06s, 940, 93», 895m, 864», S44m, 83», 79», 764», 747», 78m, 688», 668» VI b 300m, 880, 50, 80», 475vs, 460s, 0». 370m, 80», 60w, 80», 60», 095m, M65m, 060m, 045m.»Bm, 993m, 978m, 968m, 950s, 96», 905», 878», 649w, 844m, 830w, 808w, 878m, 850m, 844m, 830m, 808», 778m, 750m, 77m, 70«. 688»
7 37 IM VII b 900 ß. 50<re, B80m, 80 ß. Mofes, 400m, M70s, 3»w. 80m, 70m, I40w,!80m, 60m. 060b, KM5e. 00m, 97w, 94s, 9w, 894m, 86m, 87m, 780s, 765s. 730m, 706s Vmb 90vs. 50ve. B90m, BOOs, M80e, 60s, HK>w. 370m, B90w, 0m, 60m, 090m, 045m. 0Ow, 995w, 970w, 950m, 905w, 875w, 845m, 7S0m, 73m, 74m, 689w DC b 890 ß, 500ve, 600b, 7,., M60vs, M40vs, 400», 370s, 90w, Í80w, 48, 30s, 60m, U40s,»80s, KMOs, BOOs, 990», 96s, 945vs, 896, 883m, 8 *, 836, 600w, 784, 764w, 746, 733, 680s Nu???mulls b Tetramethy Lammonium salt
8 m7 The 80.5 MHz IIB amr spectra of (3)9. B0CH3 I. (A). and (3)7, 0B0CH3'. II,(B). measured In acetone d6. Chemical sh???s (ppm) relative to BF3 O(CH5)and coupling constants (Hz) are Indicated. Relative areas appear beneath the peaks. peaks.
9 ß.4 TP. i kw J
10 379 IM Tbc 80.5 MHz B nmr spectrum of (CH3)3N BH. are indicated. B0Cu. Chemical shifts (ppm) relative to BF3 O(CH3) Relative areas appear beneath the peeks.
11 9.4 I *.4 j It
12 379 The 80.5 MHz B nmr spectra of the B0CH ions in tetrahydrofuran prepared from ' B0CH A:,7B0CH B:,B0CH' C: 900 C after standing at room temperature for four months, D. The sharp doublet in C and D is the resonance of unreacted,b0ch. appear beneath the peaks. Chemical shifts relative to BF3.O(CH5)
13 (FROM,) 379 M
14 The 00Hz H nmr spectra of (C6Hs)4As+[7,0 (CH3)(3)7, 0B0CHJ measured at room temperature, A; measured at room temperature with heteronuclear decoupling, B; (3)7, 0B0CHJmeasured and (CH3)4N+[7, 0(CH3) at 60, C. The peaksat r 7,9 are due to acetoned6 solvent. Chemical shifts relativeto internal tetramethylsilaneappear beneath the peaks. peaks.
15 379Ml 4
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