10.1002/ejoc.202000573
European Journal of Organic Chemistry
FULL PAPER
18H), 0.55 (q, J = 7.9 Hz, 12H). 13C NMR (101 MHz, CDCl3) δ (ppm) =
6.8, 6.4. 29Si NMR (79 MHz, CDCl3) δ (ppm) = 8.9. MS (EI) m/z (rel. int.):
189 (50%), 175 (100), 146 (75), 119 (100).
MHz, CDCl3) δ (ppm) = 10.8, -0.2. MS (EI) m/z (rel. int.): 363 (M+-CH3,
30%), 263 (100), 147 (30). HR-ESI-MS (TOF) m/z: calcd.: 401.2160
(adduct [[M]Na]+); found: 401.2230 (adduct [[M]Na]+).
1,1,1-Triethyl-3,3,3-tripropyldisiloxane[83] (5ca) was obtained as
colorless oil in 90% yield. 1H NMR (400 MHz, CDCl3) δ (ppm) = 1.45 –
1.30 (m, 6H), 1.03 – 0.92 (m, 15H), 0.58 – 0.50 (m, 9H). 13C NMR (101
MHz, CDCl3) δ (ppm) = 18.6, 18.4, 16.8, 6.8, 6.4. 29Si NMR (79 MHz,
CDCl3) δ (ppm) = 8.8, 5.4. MS (EI) m/z (rel. int.): 234 (100%), 219 (50).
1,1,3,3-Tetramethyl-3-octyl-1-tert-butyldisiloxane (5fb) was obtained
as colorless oil in 97% yield. (Novel compound) 1H NMR (400 MHz,
CDCl3) δ (ppm) = 1.34 – 1.27 (m, 12H), 0.91 (t, J = 7.0 Hz, 3H), 0.88 (s,
9H), 0.56 – 0.49 (m, 2H), 0.06 (s, 6H), 0.03 (s, 6H). 13C NMR (101 MHz,
CDCl3) δ (ppm) = 33.5, 32.0, 29.4, 29.3, 25.7, 23.3, 22.7, 18.4, 18.0, 14.1,
0.4, -2.9. 29Si NMR (79 MHz, CDCl3) δ (ppm) = 9.7, 7.1. MS (EI) m/z (rel.
int.): 247 (20%), 175 (40), 149 (100), 134 (90). HR-ESI-MS (TOF) m/z:
calcd.: 303.2539 (adduct [[M]H]+); found: 303.2534 (adduct [[M]H]+).
(3-Chloropropyl)-1,1,1-triethyl-3,3-dimethyldisiloxane
(5da)
was
obtained as colorless oil in 91% yield. (Novel compound) 1H NMR (400
MHz, CDCl3) δ (ppm) = 3.53 (t, J = 7.0 Hz, 2H), 1.88 – 1.75 (m, 2H), 0.95
(t, J = 7.9 Hz, 9H), 0.67 – 0.61 (m, 2H), 0.53 (q, J = 7.9 Hz, 6H), 0.10 (s,
6H). 13C NMR (101 MHz, CDCl3) δ (ppm) = 47.9, 27.2, 16.1, 6.7, 6.3, 0.3.
29Si NMR (79 MHz, CDCl3) δ (ppm) = 10.3, 6.2. MS (EI) m/z (rel. int.):
209 (40%), 189 (100). HR-ESI-MS (TOF) m/z: calcd.: 289.1187 (adduct
[[M]H]+); found: 289.1191 (adduct [[M]H]+).
1,1,1-Trimethyl-3,3,3-tert-butoxydisiloxane[85] (5ac) was obtained as
1
colorless oil in 95% yield. H NMR (400 MHz, CDCl3) δ (ppm) = 1.30 (s,
27H), 0.15 (s, 9H). 13C NMR (101 MHz, CDCl3) δ (ppm) = 72.1, 31.3, 1.6.
29Si NMR (79 MHz, CDCl3) δ (ppm) = 8.0, -99.5. MS (EI) m/z (rel. int.):
321 (M+-CH3, 10%), 265 (30), 209 (100).
1,2-Bis((triethylsiloxy)dimethylsilyl)ethane (5ea) was obtained as
colorless oil in 62% yield. (Novel compound) H NMR (400 MHz, CDCl3)
1,1,1-Triethyl-3,3,3-tert-butoxydisiloxane (5bc) was obtained as
colorless oil in 99% yield. (Novel compound) H NMR (400 MHz, CDCl3)
1
1
δ (ppm) = 0.95 (t, J = 7.9 Hz, 18H), 0.53 (q, J = 7.9 Hz, 12H), 0.44 (s, 4H),
0.07 (s, 12H). 13C NMR (101 MHz, CDCl3) δ (ppm) =9.8, 6.8, 6.3, -0.4.
29Si NMR (79 MHz, CDCl3) δ (ppm) = 9.4, 7.5. MS (EI) m/z (rel. int.): 391
(M+-CH3, 20%), 378 (100). HR-ESI-MS (TOF) m/z: calcd.: 429.2473
(adduct [[M]Na]+); found: 429.2474 (adduct [[M]Na]+).
δ (ppm) = 1.31 (s, 27H), 1.00 (t, J = 7.9 Hz, 9H), 0.62 (q, J = 7.9 Hz, 6H).
13C NMR (101 MHz, CDCl3) δ (ppm) = 72.1, 31.3, 6.7, 6.1. 29Si NMR (79
MHz, CDCl3) δ (ppm) = 10.9, -99.6. MS (EI) m/z (rel. int.): 363 (M+-CH3,
10%), 307 (30), 251 (100), 181 (80). HR-ESI-MS (TOF) m/z: calcd.:
401.2519 (adduct [M]+); found: 401.2518 (adduct [M]+).
1,1,1-Triethyl-3,3-dimethyl-3-octyldisiloxane (5fa) was obtained as
colorless oil in 85% yield. (Novel compound) H NMR (400 MHz, CDCl3)
1,1,1-Trimethyl-3,3,3-tripropyldisiloxane[83] (5cc) was obtained as
colorless oil in 93% yield. 1H NMR (400 MHz, CDCl3) δ (ppm) = 1.43 –
1.31 (m, 6H), 0.98 (t, J = 7.3 Hz, 9H), 0.58 – 0.50 (m, 6H), 0.09 (s, 9H).
13C NMR (101 MHz, CDCl3) δ (ppm) = 18.4, 18.4, 16.8, 2.0. 29Si NMR
(79 MHz, CDCl3) δ (ppm) = 6.3, 6.1. MS (EI) m/z (rel. int.): 246 (M+, 10%),
205 (30), 161 (40), 119 (100).
1
δ (ppm) = 1.42-1.26 (m, 14H), 1.04-0.85 (m, 12H), 0.53 (q, J = 7.9 Hz,
6H), 0.07 (s, 6H). 13C NMR (101 MHz, CDCl3) δ (ppm) = 33.5, 32.0, 29.4,
29.3, 22.7, 18.5, 14.1, 6.8, 6.3, 0.4. 29Si NMR (79 MHz, CDCl3) δ (ppm) =
9.4, 6.7. MS (EI) m/z (rel. int.): 287 (M+-CH3, 100%), 175 (75). HR-ESI-
MS (TOF) m/z: calcd.: 303.2539 (adduct [[M]H]+); found: 302.2576
(adduct [[M]H]+).
1,1,1-Trimethyl-3,3,3-isobutyldisiloxane[70] (5dc) was obtained as
colorless oil in 92% yield. 1H NMR (400 MHz, CDCl3) δ (ppm) = 1.83 (dp,
J = 13.3, 6.7 Hz, 3H), 0.96 (d, J = 6.6 Hz, 18H), 0.56 (d, J = 6.9 Hz, 6H),
0.10 (s, 9H). 13C NMR (101 MHz, CDCl3) δ (ppm) = 27.6, 26.5, 24.3, 2.2.
29Si NMR (79 MHz, CDCl3) δ (ppm) = 5.7, 4.8. MS (EI) m/z (rel. int.): 233
(10%), 207 (10), 175 (40), 135 (60), 119 (100).
1,2-Bis((triethylsiloxy)-1,1,2,2-tetramethyldisilane (5ga) was obtained
as colorless oil in 77% yield. (Novel compound) 1H NMR (400 MHz,
CDCl3) δ (ppm) = 0.95 (t, J = 7.9 Hz, 18H), 0.52 (q, J = 7.9 Hz, 12H),
0.20 (s, 12H). 13C NMR (101 MHz, CDCl3) δ (ppm) = 6.8, 6.4, 2.0. 29Si
NMR (79 MHz, CDCl3) δ (ppm) = 10.5, -0.6. MS (EI) m/z (rel. int.): 217
(100%), 204 (75). HR-ESI-MS (TOF) m/z: calcd.: 379.2340 (adduct
[[M]H]+); found: 379.2357 (adduct [[M]H]+).
1,1,1-Tributyl-3,3,3-trimethyldisiloxane (5ec) was obtained as
1
colorless oil in 94% yield. (Novel compound) H NMR (400 MHz, CDCl3)
δ (ppm) = 1.40 – 1.27 (m, 12H), 0.92 (t, J = 6.9 Hz, 9H), 0.60 – 0.48 (m,
6H), 0.09 (s, 9H). 13C NMR (101 MHz, CDCl3) δ (ppm) = 26.6, 25.5, 15.3,
13.8, 2.0. 29Si NMR (79 MHz, CDCl3) δ (ppm) = 7.1, 6.0. MS (EI) m/z (rel.
int.): 233 (60%), 175 (45), 119 (100). HR-ESI-MS (TOF) m/z: calcd.:
289.2383 (adduct [M[H]]+); found: 289.2339 (adduct [M[H]]+).
1,1,3,3,3-Pentamethyl-1-tert-butyldisiloxane[84] (5ab) was obtained as
1
colorless oil in 91% yield. H NMR (400 MHz, CDCl3) δ (ppm) = 0.88 (s,
9H), 0.09 (s, 9H), 0.03 (s, 6H). 13C NMR (101 MHz, CDCl3) δ (ppm) =
25.7, 18.0, 1.9, -3.0. 29Si NMR (79 MHz, CDCl3) δ (ppm) = 9.9, 6.7. MS
(EI) m/z (rel. int.): 189 (M+-CH3, 10%), 147 (100).
1,1,1-Trimethyl-3,3,3-triphenyldisiloxane[86] (5fc) was obtained as
colorless oil in 93% yield. 1H NMR (400 MHz, CDCl3) δ (ppm) = 7.75 –
7.62 (m, 6H), 7.58 – 7.38 (m, 9H), 0.16 (s, 9H). 13C NMR (101 MHz,
CDCl3) δ (ppm) = 136.2, 135.0, 129.7, 127.7, 2.1. 29Si NMR (79 MHz,
CDCl3) δ (ppm) = 10.8, -21.6. MS (EI) m/z (rel. int.): 348 (M+, 20%), 333
(M+-CH3, 100), 255 (70).
3,3,3-Triethyl-1,1-dimethyl-1-tert-butyldisiloxane (5bb) was obtained
as colorless oil in 98% yield. (Novel compound) 1H NMR (400 MHz,
CDCl3) δ (ppm) = 0.96 (t, J = 7.9 Hz, 2H), 0.89 (s, 1H), 0.55 (q, J = 7.9
Hz, 1H), 0.05 (s, 1H). 13C NMR (101 MHz, CDCl3) δ (ppm) = 25.7, 18.2,
6.8, 6.3, -2.9. 29Si NMR (79 MHz, CDCl3) δ (ppm) = 9.5, 9.3. MS (EI) m/z
(rel. int.): 246 (M+, 20%), 220 (20), 175 (100). HR-ESI-MS (TOF) m/z:
calcd.: 247.1913 (adduct [[M]H]+); found: 247.1905 (adduct [[M]H]+).
3,3-Diisopropyl-1,1,1,5,5,5-hexamethyltrisiloxane[70]
obtained as colorless oil in 95% yield. 1H NMR (400 MHz, CDCl3) δ
(5gc)
was
1,1-Dimethyl-3,3,3-tripropyl-1-tert-butyldisiloxane (5cb) was obtained
as colorless oil in 99% yield. (Novel compound) 1H NMR (400 MHz,
CDCl3) δ (ppm) = 1.41 – 1.32 (m, 6H), 0.98 (t, J = 7.2 Hz, 9H), 0.88 (s,
9H), 0.59 – 0.51 (m, 6H), 0.03 (s, 6H). 13C NMR (101 MHz, CDCl3) δ
(ppm) = 25.8, 18.5, 18.5, 18.2, 16.8, -2.8. 29Si NMR (79 MHz, CDCl3) δ
(ppm) = 9.2, 6.1. MS (EI) m/z (rel. int.): 205 (100%), 161 (50), 147 (70),
105 (60). HR-ESI-MS (TOF) m/z: calcd.: 289.2383 (adduct [[M]H]+);
found: 289.2379 (adduct [[M]H]+).
(ppm) = 0.97 (d, J = 7.3 Hz, 12H), 0.85 – 0.73 (m, 2H), 0.13 (s, 18H). 13
C
NMR (101 MHz, CDCl3) δ (ppm) = 17.0, 13.0, 1.9. 29Si NMR (79 MHz,
CDCl3) δ (ppm) = 5.8, -23.4. MS (EI) m/z (rel. int.): 277 (M+-CH3, 60%),
249 (100), 221 (15), 207 (10).
3,3,5,5-Tetraisopropyl-1,1,1,7,7,7-hexamethyltetrasiloxane[70]
(5hc)
1
was obtained as colorless oil in 90% yield. H NMR (400 MHz, CDCl3) δ
(ppm) = 1.02 – 0.99 (m, 24H), 0.90 – 0.79 (m, 4H), 0.13 (s, 18H). 13C
NMR (101 MHz, CDCl3) δ (ppm) = 17.2, 13.4, 2.0. 29Si NMR (79 MHz,
CDCl3) δ (ppm) = 5.3, -25.3. MS (EI) m/z (rel. int.): 407 (M+-CH3, 5%),
379 (35), 263 (100), 129 (25), 73 (80).
(3-Chloropropyl)-1,1,3,3-tetramethyl-1-tert-butyldisiloxane (5db) was
obtained as colorless oil in 92% yield. (Novel compound) 1H NMR (400
MHz, CDCl3) δ (ppm) = 3.53 (t, J = 7.0 Hz, 2H), 1.87 – 1.75 (m, 2H), 0.88
(s, 9H), 0.70 – 0.59 (m, 2H), 0.10 (s, 6H), 0.04 (s, 6H). 13C NMR (101
MHz, CDCl3) δ (ppm) = 47.9, 27.1, 25.7, 18.0, 16.0, 0.3, -2.9. 29Si NMR
(79 MHz, CDCl3) δ (ppm) = 10.6, 6.6. MS (EI) m/z (rel. int.): 189 (50%),
167 (100), 147 (60). HR-ESI-MS (TOF) m/z: calcd.: 289.1187 (adduct
[[M]H]+); found: 289.1191 (adduct [[M]H]+).
1,1,1,5,5,5-Hexamethyl-3,3-diphenyltrisiloxane[70] (5ic) was obtained
as colorless oil in 94% yield. 1H NMR (400 MHz, CDCl3) δ (ppm) = 7.67 –
7.56 (m, 4H), 7.45 – 7.34 (m, 6H), 0.15 (s, 18H). 13C NMR (101 MHz,
CDCl3) δ (ppm) = 136.7, 134.2, 129.7, 127.6, 2.0. 29Si NMR (79 MHz,
CDCl3) δ (ppm) = 9.8, -47.4. MS (EI) m/z (rel. int.): 345 (M+-CH3, 100%),
283 (10), 267 (15).
1,2-Bis((dimethyl-tert-butylsiloxy)-1,1,2,2-tetramethyldisilane (5eb)
was obtained as colorless oil in 65% yield. (Novel compound) 1H NMR
(400 MHz, CDCl3) δ (ppm) = 0.88 (s, 18H), 0.20 (s, 12H), 0.03 (s, 12H).
13C NMR (101 MHz, CDCl3) δ (ppm) = 25.7, 18.0, 1.8, -2.7. 29Si NMR (79
1,1,1,3,3-Pentamethyl-3-(naphthalen-1-yl)disiloxane[70]
(5jc)
was
obtained as colorless oil in 91% yield. 1H NMR (600 MHz, CDCl3) δ
(ppm) = 8.33 – 8.30 (m, 1H), 7.96 – 7.90 (m, 2H), 7.83 – 7.77 (m, 1H),
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