Einwirkung von Grignardschem Reagens auf Alkoxylgruppen

Stereodivergent Total Synthesis of Δ9‐Tetrahydrocannabinols

“…Thus, treatment of ester 6 with excess MeMgI at 0 8C to 160 8C at reduced pressure (150 mm Hg) delivered the tertiary alcohol with concomitant removal of the phenolic methyl groups. [19] After aqueous workup and extraction, the organic phase (CH 2 Cl 2 ) was treated with ZnBr 2 , which induced aryl ether formation [20] and furnished D 9 -THC (1, all stereoisomers) in 41-65 % yield over the final sequence.…”

The Chemical Behavior of the Organoalkali Compounds.

“…The weaker Grignard reagents, also, can be kept in ether for indefinite periods. Anisóle (111) and phenetole (54), probably because of their high boiling points as well as the activation imparted by a phenyl nucleus, are cleaved at high temperature by methyl-and ethyl-magnesium iodides. Benzyl ethyl ether (112) reacts with methylmagnesium iodide to form ethylbenzene.…”