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1,6-Cycloaddition of chlorosulfonyl isocyanate to cycloheptatriene

✍ Scribed by Emil J. Moriconi; Charles F. Hummel; John F. Kelly

Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
202 KB
Volume
10
Category
Article
ISSN
0040-4039

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✦ Synopsis

Product formation, 192 kinetics3 and the prohibitions originally imposed by the Woodward-Hoffmann selection rules have suggested a 1,2-step-wise electrophilic cycloaddition of chlorosulfonyl isocyanate (CSI) to certain olefins and allenes. Recently reported observations which include: (i) the lack of rearrangement noted in the cycloaddition of CSI to bridged bi-and tricyclic olefins, 5 . . (ii) the stereospecific cycloadducts formed on addition of CSI to cis -and trans -olefins , 6,7 and (iii) the initial formation of S-11 2+2 cycloadducts between CSI and conjugated dienes, coupled with the refined Wood-1) R. Graf, Angew.

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