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Tosylate 8: Anet, F. A. L.; Bavin, P. M. G. Can. J. Chem. 1957, 35, 1081. In this work, sulfonate esters of the parent alcohols 5a-m were not investigated as starting materials for the Wagner-Meerwein rearrangement.
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18
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0042828287
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Other authors reproduced this reaction in boiling benzene and found 85% yield of dibenz[b,f]oxepin: Hess, B. A.; Bailey, A. S.; Bartusek, B.; Boekelheide, V. J. Am. Chem. Soc. 1969, 91, 1665.
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26844514391
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(a) Smith Kline & French patent; US 3100207, 1963; claims a more lengthy approach to 10-aminomethyldibenz[b,f]oxepins via 9-hydroxymethyl-9- aminoalkylxanthenes.
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20
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84982335918
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(b) Bergmann and Rabinovitz claimed the rearrangement of 9-(α-hydroxybenzyl)xanthene (5d) to 10-phenyldibenz-[b,f]oxepin but proof of structure was tentative (only IR, mp given): Bergmann, D.; Rabinovitz, M. Isr. J. Chem. 1963, 1, 125. In our hands, the substrate 5d did not rearrange, but rather gave the β-elimination product (7d, Table 1), in accordance with the theoretical calculations (vide supra, Table 3).
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(d) The 9-lithiation of xanthene was originally reported by Nakai et al.: Nakai, R.; Sugii, M.; Tomono, H. Bull. Inst. Chem. Res., Kyoto Univ. 1955, 33, 211.
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23
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84918048281
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It was also reported by Mahesh et al.: (e) Mahesh, V. B.; Seshadri, T. R. J. Sci. Ind. Res., Sect. B 1955, 14, 608.
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0007595199
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Only one other, more cumbersome method of preparation for this aldehyde (careful DIBAL-reduction of xanthene-9-carbonyl chloride) has been reported: Rochlin, E.; Rappoport, Z. J. Am. Chem. Soc. 1992, 114, 230. In our hands, this procedure gave mostly xanthone after aqueous workup and silica gel chromatography of the crude product.
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Rappoport, Z.2
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25
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26844555947
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note
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2 (1.1 equiv), -40 °C to r.t., Huenig's base (1.2 equiv), 91% yield].
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26
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26844545234
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note
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For substrates obtained using method B, it is best to avoid workup and isolation (see ref. 12), and instead use the in situ-prepared aldehyde (4) solution (see ref. 13) directly in the next step.
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28
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26844453515
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Jaguar S. S.
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32
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26844507248
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note
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The putative spirocyclopropyl cyclohexadienyl transition state dates back to the pioneering work of Winstein et al., where this transition state had been invoked to rationalize rates of solvolysis and alkyl group migration in substituted, primary phenethyl tosylates and related systems; compare:
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33
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0007178335
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