ISSN:
1600-5759
Source:
Crystallography Journals Online : IUCR Backfile Archive 1948-2001
Topics:
Chemistry and Pharmacology
,
Geosciences
,
Physics
Notes:
The thermal Diels–Alder cycloadditon reaction of diethyl 2-[cyano(toluene-4-sulfinyl)methylene]propanedioate, C16H17NO5S, with cyclopentadiene gave the pure racemates of two of the four possible diastereomers, with a complete π-facial selectivity and a high (80:20) endo/exo-sulfinyl selectivity. X-ray diffraction studies of diethyl 2-[cyano(toluene-4-sulfinyl)methylene]propanedioate and the major isomer of the cycloaddition product, namely diethyl 3-cyano-3-(toluene-4-sulfinyl)bicyclo[2.2.1]hepta-5-ene-2,2-dicarboxylate, C21H23NO5S, reveal that the conformation of the substituents on the acrylonitrile moiety produces both steric and electronic effects, which affect the stereoselectivity of the reaction.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1107/S0108270101012951
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