REACTION OF CYCLOPROPYLBENZENE AND CYCLOPROPYL PHENYL KETONE WITH SULFUR TRIOXIDE^1–3

References

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• For reasons of consistency and convenience, the phenyl ring position of the sulfonic acid group has been numbered as for the parent substrate
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• Sulfonation of 5 does not take place upon using dioxane instead of nitromethane as solvent
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• The structural assignment of 7 is based on 1H and 13C NMR (Table II), IR (CHCl3, cm−1): 3440 (OH), 1120 (SO-3), and MS (FAB−) m/z: 243 (M‐K−)
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• The addition of SO3 to the cyclopropyl moiety of cyclopropyl phenyl ketone (5) takes place preferentially at C(1′), because SO3 addition at C(2′) or C(3′) would develop in the resulting intermediate a positive charge at C(1′) i.e. directly adjacent to the positive charge at the carbonyl carbon
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