Abstract
The electron transfer photo-sensitized reaction of 7-(spirocyclopropane)quadricyclane (1) with methanol produces two rearranged mono-methanol adducts, 2 and 3, and a bis-methanol adduct, 4. The products reveal that 1·+ reacts by stereo- and regiospecific attack of methanol on one trisubstituted cyclopropane ring. The resulting free radical rapidly undergoes one or two (consecutive) cyclopropylcarbinyl to butenyl rearrangements. The mono-adducts are formed by net hydrogen abstraction, the di-adduct via a (secondary) electron transfer reaction of 3. © 1997 John Wiley & Sons, Ltd.
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