Schwartz reagent adds syn across the terminal alkene, placing zirconium at its terminal carbon and hydrogen at the substituted carbon. The organozirconium intermediate is . The two faces of the achiral starting alkene give enantiomeric organometallic intermediates.
Boron trifluoride coordinates the ether oxygen, making the benzylic C–OMe bond susceptible to cleavage. The C–Zr bond then transfers its carbon terminus intramolecularly to the benzylic carbon as the activated methoxy group departs, closing a cyclopropane. This can be represented as a concerted, strongly assisted displacement rather than requiring a freely equilibrating long-lived benzylic carbocation. hydrozirconation fixes the relative disposition of the new C–H and C–Zr bonds, and the preferred closure conformation places the bulky phenyl and methyl groups on opposite faces. The result is racemic trans-1-methyl-2-phenylcyclopropane, with much less steric crowding than the cis alternative. The ring contains the original two alkene carbons and the original benzylic carbon; no carbene carbon is added.
Schwartz reagent 2026-10-20