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85037507792
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-
Adducts from reactions of 2H-thiopyrans with dienophiles are, after desulfurization, synthetically equivalent to adducts from cis-dienes.
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-
53
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85037515044
-
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note
-
The dienes are acid sensitive and are consumed by dimerization and/or polymerization in these cases.
-
-
-
-
55
-
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37049137296
-
-
Addition of MeMgBr (1 equiv) to a toluene solution of 1a gave a clear solution only with a MeMgBr/1a ratio near 0.5; with greater or lesser amounts of MeMgBr, the mixture was cloudy. With a total ROH:MeMgBr ratio of 2, the use of pentanol (1 equiv) as a "dummy" alcohol gave a faster and more efficient reaction. Presumably, the ROH:ROMgBr ratio affects the speciation of ROMgBr. For an example of a dimeric structure, see: Moseley, P. T.; Shearer, H. M. M. J. Chem. Soc., Chem. Commun. 1968, 279-280. Reaction is much slower with MeMgCl and faster but less efficient with MeMgI.
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-
-
Moseley, P.T.1
Shearer, H.M.M.2
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56
-
-
85037504896
-
-
note
-
The regioselectivity is the ratio of ([5] + [6]):([3] + [4] + [7]).
-
-
-
-
57
-
-
85037492463
-
-
note
-
A predominance of 5/6 regioisoniers is expected on the basis of greater electron-donating properties of a methyl group vs a hydroxymethyl or methoxymethyl group. Only 3/4/7 regioisomers can form if diene and dienophile are tethered by association with a Lewis acid in the TS.
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58
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0000368939
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Toyota, M.; Wada, Y.; Fukumoto, K. Heterocycles 1993, 35, 111.
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Toyota, M.1
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59
-
-
85037512499
-
-
note
-
For example, 1a was 1.2 times more reactive than 1b toward 2a in toluene solution at 120°C as determined in a competition experiment.
-
-
-
-
60
-
-
85037495188
-
-
note
-
Chelation of 8 by 2b (i.e. 15b) prevents IMDA reaction; IMDA reaction is feasible with monodentate coordination (e.g., 14).
-
-
-
-
61
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33947297157
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Kobuke, Y.; Fueno, T.; Furukawa, Y. J. Am. Chem. Soc. 1970, 92, 6548-6553.
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Kobuke, Y.1
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62
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85037518548
-
-
note
-
1H NMR of the crude reaction mixture; yields were determined using an internal standard.
-
-
-
-
63
-
-
85037517282
-
-
note
-
2AlCl-mediated competition reactions which were faster though less reproducible.
-
-
-
-
65
-
-
85037503475
-
-
Diene 1b did not react under these conditions
-
Diene 1b did not react under these conditions.
-
-
-
-
66
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33845279009
-
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Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257-3262.
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Tripathy, R.1
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Onan, K.D.3
-
67
-
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85037507514
-
-
The C-Me configuration of 22 was not rigorously determined
-
The C-Me configuration of 22 was not rigorously determined.
-
-
-
-
68
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-
85037496810
-
-
The preparation and reactions of thiopyran dienes will be described separately
-
The preparation and reactions of thiopyran dienes will be described separately.
-
-
-
-
69
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0030908679
-
-
For similar Mg(II)-mediated [3 + 2] cycloadditions of nitrile oxides with allylic alcohols, see: (a) Kanemasa, S.; Hidetoshi, Y.; Shinsuke, K. Tetrahedron Lett. 1997, 38, 4095-4098.
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Kanemasa, S.1
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0000930644
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(b) Kanemasa, S.; Nishiuchi, M.; Kamimura, A.; Hori, K. J. Am. Chem. Soc. 1994, 116, 2324-2339.
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71
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1242311796
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For other examples of "self-assembled" templates for DA reactions, see: (a) Walter C. J.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1993, 458-460.
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(b) Walter, C. J.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 217-219.
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Walter, C.J.1
Sanders, J.K.M.2
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