Lewis‐Säure‐katalysierte Additionen 1,3‐Alkyl‐substituierter Allylchloride an Alkene

Abstract

WEINHEIM 1984HEFT 7

Rearrangement in Stereoretentive Syntheses of Menthyl Chloride from Menthol: Insight into Competing Reaction Pathways through Component Quantification Analysis

“…For the last unidentified, yet most abundant side‐product, the fragment RCH 2 CMe 2 Cl could be deduced by 2D NMR methods, which immediately points to the presence of a tertiary ψ‐menthyl chloride structure 16 (Scheme d). The excellent agreement of the relevant δ ( 13 C) shifts of 16 with those of compound 17 reported by Mayr et al secures this assignment (Scheme d) . Alkene 18 was occasionally detected as minor component of rearrangement mixtures by its characteristic doublet of septets at δ ( 1 H) 5.05 ppm that was also present in model compound 15 (Scheme b).…”

“…(c) NMR δ ( 13 C) comparison of 12 and 14 . (d) Structure of 16 , and δ ( 13 C) comparison with a related compound 17 …”