-
1
-
-
53049095447
-
-
Parts of this investigation were presented at the Scale-Up of Chemical Processes Scientific Update Conference, Boston, MA, August 29-31, 2007.
-
Parts of this investigation were presented at the "Scale-Up of Chemical Processes" Scientific Update Conference, Boston, MA, August 29-31, 2007.
-
-
-
-
3
-
-
33751017610
-
-
DelMonte, A. J.; Dowdy, E. D.; Watson, D. J. Top. Organomet. Chem. 2004, 6, 97-122.
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(2004)
Top. Organomet. Chem
, vol.6
, pp. 97-122
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DelMonte, A.J.1
Dowdy, E.D.2
Watson, D.J.3
-
4
-
-
0000527980
-
-
The reactivity order of dihalomethanes is in accordance with that of the radical halogen abstraction from these compounds. See for example: (a) Menapace, L. H, Kuivila, H. G. J. Am. Chem. Soc. 1964, 86, 3047-3051
-
The reactivity order of dihalomethanes is in accordance with that of the radical halogen abstraction from these compounds. See for example: (a) Menapace, L. H.; Kuivila, H. G. J. Am. Chem. Soc. 1964, 86, 3047-3051.
-
-
-
-
6
-
-
0001356723
-
-
(a) Friedrich, E. C.; Domek, J. M.; Pong, R. Y. J. Org. Chem. 1985, 50, 4640-4642.
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J. Org. Chem
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, pp. 4640-4642
-
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Friedrich, E.C.1
Domek, J.M.2
Pong, R.Y.3
-
9
-
-
53049110233
-
-
Bajgrowicz, J. A.; Frater, G.; EP 801049, priority 29.3.1997 to Givaudan-Roure (International) S.A. [Chem. Abstr. 127, 358652].
-
Bajgrowicz, J. A.; Frater, G.; EP 801049, priority 29.3.1997 to Givaudan-Roure (International) S.A. [Chem. Abstr. 127, 358652].
-
-
-
-
14
-
-
53049091192
-
-
Prepared from (-)-methyl chloride: (a) Krause, H. W.; Kinting, A. J. Prakt. Chem. 1980, 322, 485-486.
-
Prepared from (-)-methyl chloride: (a) Krause, H. W.; Kinting, A. J. Prakt. Chem. 1980, 322, 485-486.
-
-
-
-
15
-
-
53049104389
-
-
2 and 4 equiv of tBuMgCl (GC-conversion to the corresponding cyclopropanes after 18 h in brackets): E-2-hexenol (35%), Z-2-hexenol (65%), nonadienol (50%), geraniol (50%), nerol (10%), oct-1-en-3-ol (50%), linalool (40%), nerolidol (50%).
-
2 and 4 equiv of tBuMgCl (GC-conversion to the corresponding cyclopropanes after 18 h in brackets): E-2-hexenol (35%), Z-2-hexenol (65%), nonadienol (50%), geraniol (50%), nerol (10%), oct-1-en-3-ol (50%), linalool (40%), nerolidol (50%).
-
-
-
-
16
-
-
53049106170
-
-
Preparation of substrates 1 according to the literature: (1a)Schröder, F. WO 2006066436, priority 20.12.2005 to Givaudan S.A. Switz [Chem. Abstr. 145, 1038551
-
Preparation of substrates 1 according to the literature: (1a)Schröder, F. WO 2006066436, priority 20.12.2005 to Givaudan S.A. Switz [Chem. Abstr. 145, 1038551.
-
-
-
-
17
-
-
0000819682
-
-
(1b) Bajgrowicz, J. A.; Frank, I.; Frater, G.; Hennig, M. Helv. Chim. Acta 1998, 81, 1349-1358.
-
(1b) Bajgrowicz, J. A.; Frank, I.; Frater, G.; Hennig, M. Helv. Chim. Acta 1998, 81, 1349-1358.
-
-
-
-
18
-
-
0000252830
-
-
(1c) (a) Tamura, M.; Suzukamo, G. Tetrahedron Lett. 1981, 22, 577.
-
(1c) (a) Tamura, M.; Suzukamo, G. Tetrahedron Lett. 1981, 22, 577.
-
-
-
-
19
-
-
53049092377
-
-
Tamura, M.; Suzukamo, G.; Hirose, K. EP 29603, Sumimoto Chemical Co., 1980 [Chem. Abstr. 95, 204220].
-
(b) Tamura, M.; Suzukamo, G.; Hirose, K. EP 29603, Sumimoto Chemical Co., 1980 [Chem. Abstr. 95, 204220].
-
-
-
-
20
-
-
53049083400
-
-
1e Levorse, A. T. US 5234902, priority 28.2.1992 to International Flavors and Fragrances Inc, USA [Chem. Abstr. 119, 210271
-
(1e) Levorse, A. T. US 5234902, priority 28.2.1992 to International Flavors and Fragrances Inc., USA [Chem. Abstr. 119, 210271].
-
-
-
-
21
-
-
53049097942
-
-
(1f) Bajgrowicz, J. A.; Bringhen, A.; Frater, G.; Mueller, U. EP 743297, priority 20.11.1996 to Givaudan-Roure, Switzerland [Chem. Abstr. 126, 103856].
-
(1f) Bajgrowicz, J. A.; Bringhen, A.; Frater, G.; Mueller, U. EP 743297, priority 20.11.1996 to Givaudan-Roure, Switzerland [Chem. Abstr. 126, 103856].
-
-
-
-
22
-
-
53049085002
-
-
(1g) Kaiser, R.; Lamparsky, D. EP 45453, Givaudan L. et Cie S.A., 1980 [Chem. Abstr. 96, 199080].
-
(1g) Kaiser, R.; Lamparsky, D. EP 45453, Givaudan L. et Cie S.A., 1980 [Chem. Abstr. 96, 199080].
-
-
-
-
23
-
-
53049097040
-
-
1h Berg-Schultz, K, Bajgrowicz, J. A, Baudin, J. WO 2005026092, priority to Givaudan SA, Switz. 12.9.2003 [Chem. Abstr. 142, 336041
-
(1h) Berg-Schultz, K.; Bajgrowicz, J. A.; Baudin, J. WO 2005026092, priority to Givaudan SA, Switz. 12.9.2003 [Chem. Abstr. 142, 336041].
-
-
-
-
24
-
-
0000419371
-
-
(1i) Jacob, P., III; Brown, H. C. J. Org. Chem. 1977, 42, 579-580.
-
(1i) Jacob, P., III; Brown, H. C. J. Org. Chem. 1977, 42, 579-580.
-
-
-
-
25
-
-
53049105593
-
-
(1j) Martin, A. EP 770671, priority 30.10.1996 to Quest International B.V [Chem. Abstr. 126, 334220].
-
(1j) Martin, A. EP 770671, priority 30.10.1996 to Quest International B.V [Chem. Abstr. 126, 334220].
-
-
-
-
26
-
-
53049102991
-
DE 2430287, Texas Alkyls Inc.,
-
USA, 27544
-
Watson, S. C.; Malpass, D. B.; Yeargin, G. S. DE 2430287, Texas Alkyls Inc., USA, 1975 [Chem. Abstr. 83, 27544].
-
(1975)
Chem. Abstr
, vol.83
-
-
Watson, S.C.1
Malpass, D.B.2
Yeargin, G.S.3
-
27
-
-
53049107666
-
-
Preparation of substrate 5k: (a) Hall, J. B, Wiegers, W. J. US 4010207, International Flavors & Fragrances Inc, 1977 [Chem. Abstr. 87, 5396
-
Preparation of substrate 5k: (a) Hall, J. B.; Wiegers, W. J. US 4010207, International Flavors & Fragrances Inc., 1977 [Chem. Abstr. 87, 5396].
-
-
-
-
29
-
-
0006934066
-
-
Cheng, D.; Kreethadumrongdat, T.; Cohen, T. Org. Lett. 2001, 3, 2121-2123.
-
(2001)
Org. Lett
, vol.3
, pp. 2121-2123
-
-
Cheng, D.1
Kreethadumrongdat, T.2
Cohen, T.3
-
30
-
-
53049087042
-
-
Attempted reproduction on a 10 mmol scale and with freshly prepared zinc - copper couple under the conditions described in footnote 9 of ref 15 gave no conversion according to GC/MS.
-
Attempted reproduction on a 10 mmol scale and with freshly prepared zinc - copper couple under the conditions described in footnote 9 of ref 15 gave no conversion according to GC/MS.
-
-
-
-
31
-
-
53049103650
-
-
2-Hexylcyclopent-2-enone = Isojasmone B 11. Commercially available from Oxford Chemicals.
-
2-Hexylcyclopent-2-enone = Isojasmone B 11. Commercially available from Oxford Chemicals.
-
-
-
-
32
-
-
0141631426
-
-
Preparation of substrates 7 according to the literature: (7a) Jurkauskas, V.; Sadighi, J. P.; Buchwald, S. L. Org. Lett. 2003, 5, 2417-2420.
-
Preparation of substrates 7 according to the literature: (7a) Jurkauskas, V.; Sadighi, J. P.; Buchwald, S. L. Org. Lett. 2003, 5, 2417-2420.
-
-
-
-
33
-
-
84862569873
-
-
(7c) Berube, G.; Fallix, A. G. Can. J. Chem. 1991, 69, 77-78.
-
(7c) Berube, G.; Fallix, A. G. Can. J. Chem. 1991, 69, 77-78.
-
-
-
-
34
-
-
0000513795
-
-
(7d) Trost, B. M.; Keeley, D. E. J. Am. Chem. Soc. 1976, 98, 248-250.
-
(7d) Trost, B. M.; Keeley, D. E. J. Am. Chem. Soc. 1976, 98, 248-250.
-
-
-
-
35
-
-
0023790522
-
-
(7e) Berthelot, P.; Vaccher, C.; Devergnies, M.; Flouquet, N.; Debaert, M. J. Heterocycl. Chem. 1988, 25, 1525-1529.
-
(7e) Berthelot, P.; Vaccher, C.; Devergnies, M.; Flouquet, N.; Debaert, M. J. Heterocycl. Chem. 1988, 25, 1525-1529.
-
-
-
-
37
-
-
53049101808
-
-
Agarwal, V. K.; Thappa, R. K.; Agarwal, S. G.; Mehra, M. S.; Dhar, K. L.; Atal, C. K. Indian Perfumer 1983, 27, 112-118.
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(1983)
Indian Perfumer
, vol.27
, pp. 112-118
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-
Agarwal, V.K.1
Thappa, R.K.2
Agarwal, S.G.3
Mehra, M.S.4
Dhar, K.L.5
Atal, C.K.6
-
38
-
-
33749855504
-
-
Barras, J.-P.; Bourdin, B.; Schröder, F. Chimia 2006, 60, 574-579.
-
(2006)
Chimia
, vol.60
, pp. 574-579
-
-
Barras, J.-P.1
Bourdin, B.2
Schröder, F.3
-
41
-
-
53049089675
-
-
EP 0029603, Sumitomo Chemical Company Ltd, 1981 [Chem. Abstr. 95, 204220
-
(b) Tamura, M.; Suzukamo, G.; Hirose, K. EP 0029603, Sumitomo Chemical Company Ltd., 1981 [Chem. Abstr. 95, 204220].
-
-
-
Tamura, M.1
Suzukamo, G.2
Hirose, K.3
-
42
-
-
53049094722
-
-
and references cited therein
-
(c) Netland, P. Org. Proc. Prep. Int. 1980, 12, 261-262, and references cited therein.
-
(1980)
Org. Proc. Prep. Int
, vol.12
, pp. 261-262
-
-
Netland, P.1
-
43
-
-
53049102412
-
-
Sakaguchi, T.; Nagashima, K.; Yoshida, T. JP 49047345, Takasago Perfumery Co., Ltd., 1974 [Chem. Abstr. 81, 104862].
-
Sakaguchi, T.; Nagashima, K.; Yoshida, T. JP 49047345, Takasago Perfumery Co., Ltd., 1974 [Chem. Abstr. 81, 104862].
-
-
-
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44
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0038102923
-
-
(a) Müller, M.; Brönstrup, M.; Knopff, O.; Schulze, V.; Hoffmann, R. W. Organometallics 2003, 22, 2931-2937.
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(2003)
Organometallics
, vol.22
, pp. 2931-2937
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-
Müller, M.1
Brönstrup, M.2
Knopff, O.3
Schulze, V.4
Hoffmann, R.W.5
-
45
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-
0037827517
-
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(b) Hoffmann, R. W.; Brönstrup, M.; Müller, M. Org. Lett. 2003, 5, 313-316.
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(2003)
Org. Lett
, vol.5
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Hoffmann, R.W.1
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Müller, M.3
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47
-
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0012674339
-
-
See also: a
-
See also: (a) Ashby, E. C.; Deshpande, A. K.; Doctorovich, F. J. Org. Chem. 1994, 59, 6223-6232.
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(1994)
J. Org. Chem
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-
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Ashby, E.C.1
Deshpande, A.K.2
Doctorovich, F.3
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48
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0041812777
-
-
de Meijere, A. Ed, Georg Thieme Verlag: New York
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(b) Walton, J. C. In Houben-Weyl, Methoden der Organischen Chemie; de Meijere, A. Ed.; Georg Thieme Verlag: New York, 1997; Vol. E17c, pp 2438-2525.
-
(1997)
Houben-Weyl, Methoden der Organischen Chemie
, vol.E17c
, pp. 2438-2525
-
-
Walton, J.C.1
-
49
-
-
53049092685
-
-
Among other byproducts identified by GC/MS: 2,2,4,4-tetramethylpentane (CAS 1070-87-7), 2,2,6,6-tetramethyl-4-methyleneheptane (CAS 141-70-8), 2-tert-butyltetrahydrofuran (CAS 38624-45-2), 2,2-dimethyldecane (CAS 17302-37-3), 2,2,8-trimethyldecane (CAS 62238-01-1), 2,2-dimethylundecane (CAS 17312-64-0), tert-butyl bromide (CAS 507-19-7), 1-bromo-2,2- dimethylpropane (CAS 630-17-1), 2-bromotetrahydrofuran (CAS 59253-21-3), 3-bromo-2,2,4,4-tetramethylpentane (CAS 107713-49-5).
-
Among other byproducts identified by GC/MS: 2,2,4,4-tetramethylpentane (CAS 1070-87-7), 2,2,6,6-tetramethyl-4-methyleneheptane (CAS 141-70-8), 2-tert-butyltetrahydrofuran (CAS 38624-45-2), 2,2-dimethyldecane (CAS 17302-37-3), 2,2,8-trimethyldecane (CAS 62238-01-1), 2,2-dimethylundecane (CAS 17312-64-0), tert-butyl bromide (CAS 507-19-7), 1-bromo-2,2- dimethylpropane (CAS 630-17-1), 2-bromotetrahydrofuran (CAS 59253-21-3), 3-bromo-2,2,4,4-tetramethylpentane (CAS 107713-49-5).
-
-
-
-
50
-
-
0000458209
-
-
and references cited therein
-
Hoveyda, A. M.; Evans, D. A.; Fu, G. C. Chem. Rev 1993, 93, 1307-1370, and references cited therein.
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(1993)
Chem. Rev
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Hoveyda, A.M.1
Evans, D.A.2
Fu, G.C.3
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52
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84984236171
-
-
(1r) Ullrich, F. W.; Rotscheidt, K.; Breitmaier, E. Chem. Ber 1986, 119, 1737-1744.
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(1r) Ullrich, F. W.; Rotscheidt, K.; Breitmaier, E. Chem. Ber 1986, 119, 1737-1744.
-
-
-
-
53
-
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72049097836
-
-
(1s) Traas, P. C.; Bodens, H. Rec. Trav. Chim. Pays -Bas 1973, 92, 985-995.
-
(1s) Traas, P. C.; Bodens, H. Rec. Trav. Chim. Pays -Bas 1973, 92, 985-995.
-
-
-
-
54
-
-
53049103198
-
-
(1t) Arbuzov, B. A.; Isaeva, Z. G.; Timoshina, T. N.; Efremov, Y. Y. R. J. Org. Chem. 1993, 29, 1647-1650.
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(1t) Arbuzov, B. A.; Isaeva, Z. G.; Timoshina, T. N.; Efremov, Y. Y. R. J. Org. Chem. 1993, 29, 1647-1650.
-
-
-
-
55
-
-
0036644089
-
-
2I converted 1b similarly to 2b but without remote cyclopropanation to 2a. Evidence for exchange reactions between lithium alkoxides and Grignard reagents: Micha-Screttas, M.; Constantinos, G.; Steele, B. R.; Heropoulos, G. A. Tetrahedron Lett. 2002, 43, 4871-4873.
-
2I converted 1b similarly to 2b but without remote cyclopropanation to 2a. Evidence for exchange reactions between lithium alkoxides and Grignard reagents: Micha-Screttas, M.; Constantinos, G.; Steele, B. R.; Heropoulos, G. A. Tetrahedron Lett. 2002, 43, 4871-4873.
-
-
-
-
56
-
-
53049090140
-
-
The trans-configuration of the 5-ring carbacycles 2a and 21 cannot arise from hypothetical 8- or 10-membered carbenoid transition states.
-
The trans-configuration of the 5-ring carbacycles 2a and 21 cannot arise from hypothetical 8- or 10-membered carbenoid transition states.
-
-
-
-
57
-
-
53049087187
-
-
2 at reflux gave only traces of 8b.
-
2 at reflux gave only traces of 8b.
-
-
-
-
58
-
-
53049088509
-
-
For the mention of similar effects see ref 7b. A probable correlation between substitution pattern, conformation, and reactivity of the (homo)allylic alcohols is presently under investigation and will be communicated in due course
-
For the mention of similar effects see ref 7b. A probable correlation between substitution pattern, conformation, and reactivity of the (homo)allylic alcohols is presently under investigation and will be communicated in due course.
-
-
-
-
59
-
-
84943072946
-
-
(3c) Inhoffen, H. H.; Weissermel, K.; Quinkert, G. Chem. Ber. 1955, 88, 1313-21.
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(3c) Inhoffen, H. H.; Weissermel, K.; Quinkert, G. Chem. Ber. 1955, 88, 1313-21.
-
-
-
-
60
-
-
53049100956
-
-
3e Yoshida, T, Mookherjee, B. D, Kamath, V, Hall, J. B, Taylor, W. I, Schmitt, F. L. US 4173585, IFF, 1979 [Chem. Abstr. 92, 75959
-
(3e) Yoshida, T.; Mookherjee, B. D.; Kamath, V.; Hall, J. B.; Taylor, W. I.; Schmitt, F. L. US 4173585, IFF, 1979 [Chem. Abstr. 92, 75959].
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61
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0019928219
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(3f) Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555-563.
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(3f) Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555-563.
-
-
-
-
62
-
-
53049108988
-
-
2/tBuLi failed. Exchange reactions of lithium or magnesium alcoholates with Grignard reagents are well-known, see for example: Nützel, K. In Houben-Weyl, Methoden der Organischen Chemie; Müller, E. Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1973; XIII/2a, pp 193-194.
-
2/tBuLi failed. Exchange reactions of lithium or magnesium alcoholates with Grignard reagents are well-known, see for example: Nützel, K. In Houben-Weyl, Methoden der Organischen Chemie; Müller, E. Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1973; Vol.XIII/2a, pp 193-194.
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Sasaki, H.2
Hanai, R.3
Shibuya, A.4
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0013593664
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(b) Ratier, M.; Castaing, M.; Godet, J.-Y.; Pereyre, M. J. Chem. Res.; Miniprint 1978, 2309-2318.
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(a) Ratier, M.; Castaing, M.; Godet, J.-Y.; Pereyre, M. J. Chem. Res. (S) 1978, 179.
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Ratier, M.1
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72
-
-
53049089547
-
-
GC analysis on a 5% phenyl-95% dimethylpolysiloxane column.
-
GC analysis on a 5% phenyl-95% dimethylpolysiloxane column.
-
-
-
-
73
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0003688717
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Pretsch, E.; Bühlmann, P.; Affolter, C. Structure determination of Organic Compounds; Springer Verlag: Berlin, Germany, 2000; p 202.
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|