Additions of Organocopper Reagents and Heteroatom Nucleophiles to l-Phenylseleno-2-(p-toluenesulfonyl)ethyne. Preparation of Vinyl and Allenic Sulfones and Formation of Michael, Anti-Michael, and Rearrangement Products

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 7908-7919

  Back, Thomas G ^a   Bethell, Richard J ^a   Parvez, Masood ^a   Wehrli, Daniel ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000566731     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981224r     Document Type: Article

References (74)

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60. (a) The structure of 21 was tentatively shown as the antiMichael adduct in our preliminary communication (ref 7), based on NMR data. Its X-ray crystal structure clearly indicates that it is the rearranged product shown here,
61. (b) Very recently, 28 of unspecified geometry was also obtained from the reaction of a p-toluenesulfonylalkynyliodonium inflate with benzeneselenolate anion, presumably via the formation of 4 as an intermediate: Stang, P. J.; Murch, P. Synthesis 1997, 1378.
62. We have also noted that cycloadditions of 4 often show the opposite regiochemistry from that expected of normal acetylenic sulfones, again pointing to a strong directing effect of the selenium moiety. Back, T. G.; Wehrli, D. Synlett 1995, 1123.
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64. The cis geometry of 45 and 46 was confirmed by typical cis coupling constants (J = 5.1 and 8.5 Hz, respectively) while cis-47 is a known compound that also had appropriate t/s-H couplings (see Experimental Section). The assignment of the cis geometry to adduct 44 is tentative and based largely on analogy with 45-47. Neither the olefinic coupling constant (J = 12.9 Hz) nor NOE experiments gave conclusive evidence of cis-trans configuration. A referee has suggested that this may be due to rapid equilibration between cis and trans isomers in the case of 44.
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69. NMR analysis of the crude reaction mixture indicated signals that could be due to the presence of small amounts (ca. 10% relative to the major isomer) of the other geometric isomer, indicating that the substitution reaction is not completely stereospecific under these conditions.
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