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1
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-
78649680123
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-
Cee, V. J.; Deak, H. L.; Du, B.; Geuns-Meyer, S. D.; Hodous, B. L.; Nguyen, H. N.; Olivieri, P. R.; Patel, V. F.; Romero, K.; Schenkel, L. Chem. Abstr. 2007, 147, 235186
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(2007)
Chem. Abstr.
, vol.147
, pp. 235186
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Cee, V.J.1
Deak, H.L.2
Du, B.3
Geuns-Meyer, S.D.4
Hodous, B.L.5
Nguyen, H.N.6
Olivieri, P.R.7
Patel, V.F.8
Romero, K.9
Schenkel, L.10
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3
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4243418505
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-
For alternate synthesis, see
-
For alternate synthesis, see: Iwase, N.; Morinaka, Y.; Tamao, Y.; Kanayama, T.; Yamada, K. Chem. Abstr. 1993, 119, 249963
-
(1993)
Chem. Abstr.
, vol.119
, pp. 249963
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Iwase, N.1
Morinaka, Y.2
Tamao, Y.3
Kanayama, T.4
Yamada, K.5
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7
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0001207959
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Gronowitz, S.; Cederlund, B.; Hornfeldt, A.-B. Chem. Scr. 1974, 5, 217-226
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(1974)
Chem. Scr.
, vol.5
, pp. 217-226
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Gronowitz, S.1
Cederlund, B.2
Hornfeldt, A.-B.3
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9
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39049124232
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Alorati, A. D.; Bio, M. M.; Brands, K. M. J.; Cleator, E.; Davies, A. J.; Wilson, R. D.; Wise, C. S. Org. Process Res. Dev. 2007, 11, 637-641
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(2007)
Org. Process Res. Dev.
, vol.11
, pp. 637-641
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Alorati, A.D.1
Bio, M.M.2
Brands, K.M.J.3
Cleator, E.4
Davies, A.J.5
Wilson, R.D.6
Wise, C.S.7
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10
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35348825460
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-
Klingensmith, L. M.; Bio, M. M.; Moniz, G. A. Tetrahedron Lett. 2007, 48, 8242-8245
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(2007)
Tetrahedron Lett.
, vol.48
, pp. 8242-8245
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-
Klingensmith, L.M.1
Bio, M.M.2
Moniz, G.A.3
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11
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78649640494
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-
Regioisomeric ratio upon reaction with phthalic anhydride (not a direct measurement of deprotonation)
-
Regioisomeric ratio upon reaction with phthalic anhydride (not a direct measurement of deprotonation).
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-
-
-
12
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78649649320
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-
13C NMR indicates that isolated keto acid 4 exists as the open form shown in Scheme 2 and side product 5 exists as the closed lactone form
-
13C NMR indicates that isolated keto acid 4 exists as the open form shown in Scheme 2 and side product 5 exists as the closed lactone form.
-
-
-
-
13
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0013176386
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-
Handlíř, K.; Holeček, J.; Beneš, L. Collect. Czech. Chem. Commun. 1985, 50, 2422-2430
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(1985)
Collect. Czech. Chem. Commun.
, vol.50
, pp. 2422-2430
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-
Handlíř, K.1
Holeček, J.2
Beneš, L.3
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14
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78649673194
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Using the solvent DME resulted in a 1:1.4 ratio of 4: 5, possibly indicating a destabilization of alkoxide 7b
-
Using the solvent DME resulted in a 1:1.4 ratio of 4: 5, possibly indicating a destabilization of alkoxide 7b.
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-
-
-
15
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33846031566
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Lin, W.; Baron, O.; Knochel, P. Org. Lett. 2006, 8, 5673-5676
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(2006)
Org. Lett.
, vol.8
, pp. 5673-5676
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-
Lin, W.1
Baron, O.2
Knochel, P.3
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17
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53249110866
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Rohbogner, C. J.; Clososki, G. C.; Knochel, P. Angew. Chem., Int. Ed. 2008, 47, 1503-1507
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(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 1503-1507
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-
Rohbogner, C.J.1
Clososki, G.C.2
Knochel, P.3
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18
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33746216322
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Krasovskiy, A.; Krasovskaya, V.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 2958-2961
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(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 2958-2961
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Krasovskiy, A.1
Krasovskaya, V.2
Knochel, P.3
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19
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35048862730
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Clososki, G. C.; Rohbogner, C. J.; Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7681-7684
-
(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 7681-7684
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Clososki, G.C.1
Rohbogner, C.J.2
Knochel, P.3
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22
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78649667243
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For a relevant discussion, see
-
For a relevant discussion, see
-
-
-
-
23
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33846064670
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Shen, K.; Fu, Y.; Li, J.-N.; Liu, L.; Guo, Q.-X. Tetrahedron 2007, 63, 1568-1576
-
(2007)
Tetrahedron
, vol.63
, pp. 1568-1576
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-
Shen, K.1
Fu, Y.2
Li, J.-N.3
Liu, L.4
Guo, Q.-X.5
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24
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78649638114
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3OD, indicating competitive electrophilic iodination of the Me-substituted alkene
-
3OD, indicating competitive electrophilic iodination of the Me-substituted alkene.
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-
-
-
25
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78649677732
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No change in rate was observed with i PrMgCl.LiCl instead of i -PrMgCl
-
No change in rate was observed with i PrMgCl.LiCl instead of i -PrMgCl.
-
-
-
-
26
-
-
78649659611
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-
Residual n -hexane complicated the through-process synthesis of phthalazinone 6 (oiling during crystallization) and was abandoned for the synthesis of this particular target. Further investigation of n -hexylmagnesium chloride in similar applications is underway
-
Residual n -hexane complicated the through-process synthesis of phthalazinone 6 (oiling during crystallization) and was abandoned for the synthesis of this particular target. Further investigation of n -hexylmagnesium chloride in similar applications is underway.
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-
-
-
27
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78649658467
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For reversible metalation of other heterocycles, see
-
For reversible metalation of other heterocycles, see
-
-
-
-
29
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33845279383
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Trécourt, F.; Mallet, M.; Marsais, F.; Quéguiner, G. J. Org. Chem. 1988, 53, 1367-1371
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(1988)
J. Org. Chem.
, vol.53
, pp. 1367-1371
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Trécourt, F.1
Mallet, M.2
Marsais, F.3
Quéguiner, G.4
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30
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77952032691
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Viciu, M. S.; Gupta, L.; Collum, D. B. J. Am. Chem. Soc. 2010, 132, 6361-6365
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(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 6361-6365
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Viciu, M.S.1
Gupta, L.2
Collum, D.B.3
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31
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78649649319
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Use of excess i -PrMgCl (≥1.3 equiv) is detrimental to phthalic anhydride addition, producing a side product from isopropyl incorporation into keto acid product 4
-
Use of excess i -PrMgCl (≥1.3 equiv) is detrimental to phthalic anhydride addition, producing a side product from isopropyl incorporation into keto acid product 4.
-
-
-
-
32
-
-
78649639126
-
-
Magnesium or lithium aggregates have been implicated in reversible metallations of this type. See references 16a-16c and references within for more details
-
Magnesium or lithium aggregates have been implicated in reversible metallations of this type. See references 16a-16c and references within for more details.
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-
-
-
33
-
-
78649666722
-
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The 98% conversion is calculated on the basis of the limiting reagent i -PrMgCl
-
The 98% conversion is calculated on the basis of the limiting reagent i -PrMgCl.
-
-
-
-
34
-
-
78649645313
-
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Yield and equivalents are based on the limiting reagent phthalic anhydride
-
Yield and equivalents are based on the limiting reagent phthalic anhydride.
-
-
-
-
35
-
-
0028088049
-
-
See Supporting Information for a detailed procedure
-
Lin, H.-S.; Paquette, L. A. Synth. Commun. 1994, 24, 2503-2506. See Supporting Information for a detailed procedure
-
(1994)
Synth. Commun.
, vol.24
, pp. 2503-2506
-
-
Lin, H.-S.1
Paquette, L.A.2
-
36
-
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78649663341
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-
In a power compensation calorimetry experiment conducted at 10°C isothermal, quenching the reaction with water (4 volumes over 1 h, 60.6 mmol scale) resulted in a 74 kJ/mol exotherm, uncorrected for heat of mixing
-
In a power compensation calorimetry experiment conducted at 10°C isothermal, quenching the reaction with water (4 volumes over 1 h, 60.6 mmol scale) resulted in a 74 kJ/mol exotherm, uncorrected for heat of mixing.
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-
-
-
37
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78649640493
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-
This reaction proceeds below the flash point of 35% hydrazine/water (112.7°C) and below the boiling point of a hydrazine/water azeotrope (120.3°C). DSC and ARC scanning of the reaction components at 300 and 250°C, respectively, showed no unsafe thermodynamic events
-
This reaction proceeds below the flash point of 35% hydrazine/water (112.7°C) and below the boiling point of a hydrazine/water azeotrope (120.3°C). DSC and ARC scanning of the reaction components at 300 and 250°C, respectively, showed no unsafe thermodynamic events.
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