CYCLOADDITIONS .44. 2,3-DONOR-ACCEPTOR-SUBSTITUTED 1,3-BUTADIENES - SYNTHESIS BY SO2-EXTRUSION FROM 3-SULFOLENES AND DIELS-ALDER REACTIONS

HOFFMANN R, Mattay J, BANNING A, RODEWALD U, MOLLER MM (1994)
Journal für praktische Chemie 336(4): 343-349.

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Abstract
The thermal extrusion of SO2 from disubstituted 3-sulfolenes 3 leads to 2,3-donor-acceptor-substituted 1,3-butadienes 4. These dienes react with acrylic acid ester and ethyl vinyl ether to the corresponding Diels-Alder adducts 5 and 6 and with themselves to the cyclic dimerization products 7 and 8. The regiochemistry of the cycloadducts has been determined by chemical- and NMR-methods. The pyrolysis of 3-sulfolene 11 afforded the thiolactone 13 whose structure has been verified by X-ray diffraction analysis. In addition, the influence of Lewis acid catalysts on the Diels-Alder reaction and an approach to transition state calculation by means of the semiempirical AM 1 method has also been investigated.
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HOFFMANN R, Mattay J, BANNING A, RODEWALD U, MOLLER MM. CYCLOADDITIONS .44. 2,3-DONOR-ACCEPTOR-SUBSTITUTED 1,3-BUTADIENES - SYNTHESIS BY SO2-EXTRUSION FROM 3-SULFOLENES AND DIELS-ALDER REACTIONS. Journal für praktische Chemie. 1994;336(4):343-349.
HOFFMANN, R., Mattay, J., BANNING, A., RODEWALD, U., & MOLLER, M. M. (1994). CYCLOADDITIONS .44. 2,3-DONOR-ACCEPTOR-SUBSTITUTED 1,3-BUTADIENES - SYNTHESIS BY SO2-EXTRUSION FROM 3-SULFOLENES AND DIELS-ALDER REACTIONS. Journal für praktische Chemie, 336(4), 343-349.
HOFFMANN, R., Mattay, J., BANNING, A., RODEWALD, U., and MOLLER, M. M. (1994). CYCLOADDITIONS .44. 2,3-DONOR-ACCEPTOR-SUBSTITUTED 1,3-BUTADIENES - SYNTHESIS BY SO2-EXTRUSION FROM 3-SULFOLENES AND DIELS-ALDER REACTIONS. Journal für praktische Chemie 336, 343-349.
HOFFMANN, R., et al., 1994. CYCLOADDITIONS .44. 2,3-DONOR-ACCEPTOR-SUBSTITUTED 1,3-BUTADIENES - SYNTHESIS BY SO2-EXTRUSION FROM 3-SULFOLENES AND DIELS-ALDER REACTIONS. Journal für praktische Chemie, 336(4), p 343-349.
R. HOFFMANN, et al., “CYCLOADDITIONS .44. 2,3-DONOR-ACCEPTOR-SUBSTITUTED 1,3-BUTADIENES - SYNTHESIS BY SO2-EXTRUSION FROM 3-SULFOLENES AND DIELS-ALDER REACTIONS”, Journal für praktische Chemie, vol. 336, 1994, pp. 343-349.
HOFFMANN, R., Mattay, J., BANNING, A., RODEWALD, U., MOLLER, M.M.: CYCLOADDITIONS .44. 2,3-DONOR-ACCEPTOR-SUBSTITUTED 1,3-BUTADIENES - SYNTHESIS BY SO2-EXTRUSION FROM 3-SULFOLENES AND DIELS-ALDER REACTIONS. Journal für praktische Chemie. 336, 343-349 (1994).
HOFFMANN, R, Mattay, Jochen, BANNING, A, RODEWALD, U, and MOLLER, MM. “CYCLOADDITIONS .44. 2,3-DONOR-ACCEPTOR-SUBSTITUTED 1,3-BUTADIENES - SYNTHESIS BY SO2-EXTRUSION FROM 3-SULFOLENES AND DIELS-ALDER REACTIONS”. Journal für praktische Chemie 336.4 (1994): 343-349.
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