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37049103756
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The reaction of phthalimidesulfenyl chloride with alkenes is a quantitative process leading to precursors of episulfides: M. U. Bombala, S. V. Ley, J. Chem. Soc., Perkin Trans. 1 1979, 3013-3016.
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15
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19444372124
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note
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All attempts to obtain the acid 3b from the corresponding ethyl ester were unfruitful, whether under acidic or basic conditions.
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16
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19444387821
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note
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As a further demonstration of the effectiveness of oxidation at sulfur in controlling the retro Diels-Alder processes, sulfides 3a and 7a and 7b are perfectly stable in refluxing THF.
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17
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0000530970
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[11a] R. Y. Ning, P. B. Madan, J. F. Blount, R. I. Fryer, J. Org. Chem. 1976, 41, 3406-3409. -
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19
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19444377568
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note
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The rate of formation of compound 12a from 10b can be increased by heating 9a in benzene at 80 °C (72 h vs. 240 h): however, under these conditions, the yield of 12a is lower (15%) and some quantities of the corresponding β-keto ester (allyl-3-oxobutanoate) can be isolated.
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20
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19444387152
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note
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Also in this case, using a mixture of cis and trans sulfoxides, we can appreciate the quite fast reaction of cis isomer to give the final product and/or the trans sulfoxide.
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21
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19444373524
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AM1 Molecular mechanics semi-empirical calculation
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AM1 Molecular mechanics semi-empirical calculation.
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22
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0032557197
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E. Vedejs, R. J. Galante, P. G. Goekjian, J. Am. Chem. Soc. 1998, 120, 3613-3622.
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24
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0033612368
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0001027385
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Kim, S.4
Kessabi, J.5
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26
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19444374560
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note
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Unfortunately, the quality of crystals of compounds 12a and 12b does not allow an X-ray analysis. Moreover, probably because of a retro Diels-Alders process and/or loss of sulfur monoxide, derivatives 12 underwent decomposition on heating without any defined melting point.
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