-
2
-
-
24044531286
-
-
Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188-5240
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 5188-5240
-
-
Bräse, S.1
Gil, C.2
Knepper, K.3
Zimmermann, V.4
-
5
-
-
0009716687
-
-
Gray, P.; Waddington, T. C. Proc. R. Soc., London A 1957, 241, 110-121
-
(1957)
Proc. R. Soc., London A
, vol.241
, pp. 110-121
-
-
Gray, P.1
Waddington, T.C.2
-
7
-
-
0038652257
-
-
Tomlinson, W. R.; Ottoson, K. G.; Audrieth, L. F. J. Am. Chem. Soc. 1949, 71, 375-376
-
(1949)
J. Am. Chem. Soc.
, vol.71
, pp. 375-376
-
-
Tomlinson, W.R.1
Ottoson, K.G.2
Audrieth, L.F.3
-
8
-
-
33748421739
-
-
Talaward, M. B.; Agrawal, A. P.; Anniyappan, M.; Wani, D. S.; Bansode, M. K.; Gore, G. M. J. Hazard. Mater. 2006, 137, 1074-1078
-
(2006)
J. Hazard. Mater.
, vol.137
, pp. 1074-1078
-
-
Talaward, M.B.1
Agrawal, A.P.2
Anniyappan, M.3
Wani, D.S.4
Bansode, M.K.5
Gore, G.M.6
-
9
-
-
0001147897
-
-
Hassner, A.; Stern, M.; Gottlieb, H. E.; Frolow, F. J. Org. Chem. 1990, 55, 2304-2306
-
(1990)
J. Org. Chem.
, vol.55
, pp. 2304-2306
-
-
Hassner, A.1
Stern, M.2
Gottlieb, H.E.3
Frolow, F.4
-
12
-
-
0010351234
-
-
The heuristic of violent decomposition expected for azido compounds having a (C + O)/N ratio of <3 is typically used as a qualitative measure of risk: Smith, P. A. S. The Chemistry of Open-Chain Organic Nitrogen Compounds; W. A. Benjamin Inc.: New York, USA, 1966; Vol. II, pp 211-256.
-
(1966)
The Chemistry of Open-Chain Organic Nitrogen Compounds
, vol.2
, pp. 211-256
-
-
Smith, P.A.S.1
-
13
-
-
84891572017
-
-
Nonetheless, reactions involving azide intermediates must be first conducted in small laboratory scale and evaluated with specialized equipment before considering additional development. For a discussion: Keicher, T.; Löbbecke, S. Organic Azides: Synthesis and Applications; Bräse, S.; Banert, K., Eds.; Wiley-VCH: Weinheim, 2010; pp 3-27.
-
(2010)
Organic Azides: Synthesis and Applications
, pp. 3-27
-
-
Keicher, T.1
Löbbecke, S.2
-
14
-
-
72449206576
-
-
See also: Tsuritani, T.; Mizuno, H.; Nonoyama, N.; Kii, S.; Akao, A.; Sato, K.; Yasuda, N.; Mase, T. Org. Process Res. Dev. 2009, 13, 1407-1412
-
(2009)
Org. Process Res. Dev.
, vol.13
, pp. 1407-1412
-
-
Tsuritani, T.1
Mizuno, H.2
Nonoyama, N.3
Kii, S.4
Akao, A.5
Sato, K.6
Yasuda, N.7
Mase, T.8
-
18
-
-
84871584305
-
-
NIOSH (National Institute for Occupational Safety and Health), International Chemical Safety Cards No. 09050, Recommended Exposure Limits (REL)
-
NIOSH (National Institute for Occupational Safety and Health), International Chemical Safety Cards No. 09050, Recommended Exposure Limits (REL), 1997.
-
(1997)
-
-
-
20
-
-
0342598943
-
-
Bormett, R. W.; Asher, S. A.; Larkin, P. J.; Gustafson, W. G.; Ragunathan, N.; Freedman, T. B.; Nafie, L. A.; Balasubramanian, S.; Boxer, S. G.; Yu, N.-T.; Gersonde, K.; Noble, R. W.; Springer, B. A.; Sligar, S. G. J. Am. Chem. Soc. 1992, 114, 6864-6887
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 6864-6887
-
-
Bormett, R.W.1
Asher, S.A.2
Larkin, P.J.3
Gustafson, W.G.4
Ragunathan, N.5
Freedman, T.B.6
Nafie, L.A.7
Balasubramanian, S.8
Boxer, S.G.9
Yu, N.-T.10
Gersonde, K.11
Noble, R.W.12
Springer, B.A.13
Sligar, S.G.14
-
22
-
-
33745044919
-
-
Bowler, M. W.; Montgomery, M. G.; Leslie, A. G. W.; Walker, J. E. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 8646-8649
-
(2006)
Proc. Natl. Acad. Sci. U.S.A.
, vol.103
, pp. 8646-8649
-
-
Bowler, M.W.1
Montgomery, M.G.2
Leslie, A.G.W.3
Walker, J.E.4
-
25
-
-
65949090271
-
-
Kopach, M. E.; Murray, M. M.; Braden, T. M.; Kobierski, M. E.; Williams, O. L. Org. Process Res. Dev. 2009, 13, 152-160
-
(2009)
Org. Process Res. Dev.
, vol.13
, pp. 152-160
-
-
Kopach, M.E.1
Murray, M.M.2
Braden, T.M.3
Kobierski, M.E.4
Williams, O.L.5
-
26
-
-
77956895241
-
-
Gutmann, B.; Roduit, J.-P.; Roberge, D.; Kappe, O. Angew. Chem., Int. Ed. 2010, 49, 7101-7105
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 7101-7105
-
-
Gutmann, B.1
Roduit, J.-P.2
Roberge, D.3
Kappe, O.4
-
27
-
-
79953247969
-
-
Palde, P. B.; Jamison, T. F. Angew. Chem., Int. Ed. 2011, 50, 3525-3528
-
(2011)
Angew. Chem., Int. Ed.
, vol.50
, pp. 3525-3528
-
-
Palde, P.B.1
Jamison, T.F.2
-
28
-
-
81255179367
-
-
Gutmann, B.; Roduit, J.-P.; Roberge, D.; Kappe, C. O. Chem.-Eur. J. 2011, 17, 13146-13150
-
(2011)
Chem. - Eur. J.
, vol.17
, pp. 13146-13150
-
-
Gutmann, B.1
Roduit, J.-P.2
Roberge, D.3
Kappe, C.O.4
-
29
-
-
84857885274
-
-
Gutmann, B.; Obermayer, D.; Roduit, R.; Roberge, D. M.; Kappe, C. O. J. Flow. Chem. 2012, 1, 8-19
-
(2012)
J. Flow. Chem.
, vol.1
, pp. 8-19
-
-
Gutmann, B.1
Obermayer, D.2
Roduit, R.3
Roberge, D.M.4
Kappe, C.O.5
-
31
-
-
72449146232
-
-
Alimardanov, A.; Nikitenko, A.; Connolly, T. J.; Feigelson, G.; Chan, A. W.; Ding, Z.; Ghosh, M.; Shi, X.; Ren, J.; Hansen, E.; Farr, R.; MacEwan, M.; Tadayon, S.; Springer, D. M.; Kreft, A. F.; Ho, D. M.; Potoski, J. R. Org. Process Res. Dev. 2009, 13, 1161-1168
-
(2009)
Org. Process Res. Dev.
, vol.13
, pp. 1161-1168
-
-
Alimardanov, A.1
Nikitenko, A.2
Connolly, T.J.3
Feigelson, G.4
Chan, A.W.5
Ding, Z.6
Ghosh, M.7
Shi, X.8
Ren, J.9
Hansen, E.10
Farr, R.11
MacEwan, M.12
Tadayon, S.13
Springer, D.M.14
Kreft, A.F.15
Ho, D.M.16
Potoski, J.R.17
-
32
-
-
77950139237
-
-
Connolly, T. J.; Hansen, E. C.; MacEwan, M. F. Org. Process Res. Dev. 2010, 14, 466-469
-
(2010)
Org. Process Res. Dev.
, vol.14
, pp. 466-469
-
-
Connolly, T.J.1
Hansen, E.C.2
MacEwan, M.F.3
-
33
-
-
33645544385
-
-
Wiss, J.; Fleury, C.; Onken, U. Org. Process Res. Dev. 2006, 10, 349-353
-
(2006)
Org. Process Res. Dev.
, vol.10
, pp. 349-353
-
-
Wiss, J.1
Fleury, C.2
Onken, U.3
-
34
-
-
34547560379
-
-
Chen, C.-Y.; Frey, L. F.; Shultz, S.; Wallace, D. J.; Marcantonio, K.; Payack, J. F.; Vazquez, E.; Springfield, S. A.; Zhou, G.; Liu, P.; Kieczykowski, G. R.; Chen, A. M.; Phenix, B. D.; Singh, U.; Strine, J.; Izzo, B.; Krska, S. W. Org. Process Res. Dev. 2007, 11, 616-623
-
(2007)
Org. Process Res. Dev.
, vol.11
, pp. 616-623
-
-
Chen, C.-Y.1
Frey, L.F.2
Shultz, S.3
Wallace, D.J.4
Marcantonio, K.5
Payack, J.F.6
Vazquez, E.7
Springfield, S.A.8
Zhou, G.9
Liu, P.10
Kieczykowski, G.R.11
Chen, A.M.12
Phenix, B.D.13
Singh, U.14
Strine, J.15
Izzo, B.16
Krska, S.W.17
-
35
-
-
66249138465
-
-
Wilson, R. D.; Cleator, E.; Ashwood, M. S.; Bio, M. M.; Brands, K. M. J.; Davies, A. J.; Dolling, U.-H.; Emerson, K. M.; Gibb, A. D.; Hands, D.; McKeown, A. E.; Oliver, S. F.; Reamer, R. A.; Sheen, F. J.; Stewart, G. W.; Zhou, G. X. Org. Process Res. Dev. 2009, 13, 543-547
-
(2009)
Org. Process Res. Dev.
, vol.13
, pp. 543-547
-
-
Wilson, R.D.1
Cleator, E.2
Ashwood, M.S.3
Bio, M.M.4
Brands, K.M.J.5
Davies, A.J.6
Dolling, U.-H.7
Emerson, K.M.8
Gibb, A.D.9
Hands, D.10
McKeown, A.E.11
Oliver, S.F.12
Reamer, R.A.13
Sheen, F.J.14
Stewart, G.W.15
Zhou, G.X.16
-
36
-
-
79960483896
-
-
Wallace, D. J.; Baxter, C. A.; Brands, K. J. M.; Bremeyer, N.; Desmond, R.; Emerson, K. M.; Foley, J.; Fernández, P.; Hu, W.; Keen, S. P.; Mullens, P.; Muzzio, D.; Sajonz, P.; Tan, L.; Wilson, R. D.; Zhou, G.; Zhou, G. Org. Process Res. Dev. 2011, 15, 831-840
-
(2011)
Org. Process Res. Dev.
, vol.15
, pp. 831-840
-
-
Wallace, D.J.1
Baxter, C.A.2
Brands, K.J.M.3
Bremeyer, N.4
Desmond, R.5
Emerson, K.M.6
Foley, J.7
Fernández, P.8
Hu, W.9
Keen, S.P.10
Mullens, P.11
Muzzio, D.12
Sajonz, P.13
Tan, L.14
Wilson, R.D.15
Zhou, G.16
Zhou, G.17
-
37
-
-
80053010113
-
-
Girardin, M.; Dolman, S. J.; Lauzon, S.; Oullet, S. G.; Hughes, G.; Fernández, P.; Zhou, G.; O'Shea, P. D. Org. Process Res. Dev. 2011, 15, 1073-1080
-
(2011)
Org. Process Res. Dev.
, vol.15
, pp. 1073-1080
-
-
Girardin, M.1
Dolman, S.J.2
Lauzon, S.3
Oullet, S.G.4
Hughes, G.5
Fernández, P.6
Zhou, G.7
O'Shea, P.D.8
-
38
-
-
79959376296
-
-
Scott, J. P.; Alam, M.; Bremeyer, N.; Goodyear, A.; Lam, T.; Wilson, R. D.; Zhou, G. Org. Process Res. Dev. 2011, 15, 1116-1123
-
(2011)
Org. Process Res. Dev.
, vol.15
, pp. 1116-1123
-
-
Scott, J.P.1
Alam, M.2
Bremeyer, N.3
Goodyear, A.4
Lam, T.5
Wilson, R.D.6
Zhou, G.7
-
39
-
-
84857530344
-
-
Zhou, G.; Emerson, K.; Majusiak, E.; Anderson, C.; Sudah, O. Org. Process Res. Dev. 2012, 16, 204-213
-
(2012)
Org. Process Res. Dev.
, vol.16
, pp. 204-213
-
-
Zhou, G.1
Emerson, K.2
Majusiak, E.3
Anderson, C.4
Sudah, O.5
-
43
-
-
46449138435
-
-
Wiley-VCH: ARC: Accelerating Rate Calorimeter. C80: Setaram C80 Calvet Calorimeter. ADT 24: Temperature at which time to maximum rate at adiabatic conditions is 24 h. AKTS: Advanced Kinetics and Technology Solutions Thermokinetics Software
-
Stoessel, F. Thermal Safety of Chemical Processes: Risk Assessment and Process Design; Wiley-VCH: 2008; pp 66-67. ARC: Accelerating Rate Calorimeter. C80: Setaram C80 Calvet Calorimeter. ADT 24: Temperature at which time to maximum rate at adiabatic conditions is 24 h. AKTS: Advanced Kinetics and Technology Solutions Thermokinetics Software.
-
(2008)
Thermal Safety of Chemical Processes: Risk Assessment and Process Design
, pp. 66-67
-
-
Stoessel, F.1
-
44
-
-
84989509374
-
-
Low temperatures are also required in order to prevent a [3,3]-sigmatropic rearrangement that results in formation of the 1,2-disubstituted adduct. While this is more pronounced for the five-membered ring series, Trost, B. M.; Stenkamp, D.; Pulley, S. R. Chem.-Eur. J. 1995, 1, 568-562, we also observed it for the six-membered ring upon holding the reaction mixture at room temperature for extended periods of time.
-
(1995)
Chem. - Eur. J.
, vol.1
, pp. 568-562
-
-
Trost, B.M.1
Stenkamp, D.2
Pulley, S.R.3
-
45
-
-
0000363937
-
-
Alternative conditions for the reduction of the allylic azide were evaluated including hydrogenation and thiol-based methods. Nevertheless, the Staudinger reaction proved superior in terms of rate, overall impurity profile, and process control. Different phosphines can be used in the Staudinger reaction: Gololobov, Y. G.; Zhmurova, I. N.; Kasukn, I. F. Tetrahedron 1980, 37, 437-472
-
(1980)
Tetrahedron
, vol.37
, pp. 437-472
-
-
Gololobov, Y.G.1
Zhmurova, I.N.2
Kasukn, I.F.3
-
46
-
-
0035537542
-
-
IPAc was chosen as the solvent for the Boc-protection to facilitate the solvent exchanged to IPA required for the crystallization and to minimize unit operations and cycle time. Chen, C.-K.; Singh, A. K. Org. Process Res. Dev. 2001, 5, 508-513.
-
(2001)
Org. Process Res. Dev.
, vol.5
, pp. 508-513
-
-
Chen, C.-K.1
Singh, A.K.2
-
49
-
-
84871548363
-
-
Ertel, D.; Schmieder, A.; Stollenwerk, H. Nukl. Ensorgung 1989, 4, 107-119
-
(1989)
Nukl. Ensorgung
, vol.4
, pp. 107-119
-
-
Ertel, D.1
Schmieder, A.2
Stollenwerk, H.3
-
52
-
-
37149009974
-
-
Wiss, J.; Fleury, C.; Heuberger, C.; Onken, U.; Glor, M. Org. Process Res. Dev. 2007, 11, 1096-1103
-
(2007)
Org. Process Res. Dev.
, vol.11
, pp. 1096-1103
-
-
Wiss, J.1
Fleury, C.2
Heuberger, C.3
Onken, U.4
Glor, M.5
-
54
-
-
33847088763
-
-
Wilhelm, E.; Battino, R.; Wilcock, R. J. Chem. Rev. 1977, 77, 219-262
-
(1977)
Chem. Rev.
, vol.77
, pp. 219-262
-
-
Wilhelm, E.1
Battino, R.2
Wilcock, R.J.3
|