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The stereochemistry of the Grignard — Ortho ester reaction revisited: Regioselective endocyclic cleavage in the reaction of Grignard reagents with cis-2-methoxy-4-methyl-1,3-dioxane

✍ Scribed by William F. Bailey; Allan A. Croteau; Alberto D. Rivera

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
304 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reaction of cis-2-methoxy-4-methyl-1,3-dioxane (4) with Grignard reagents proceeds in a totally regioselective manner via rupture of the less congested C(2)-0(1) bond remote from the 4-methyl substituent. The analogous r-2-methoxy-cis-4,cis-6-dimethyi-l,3dioxane

(2) is totally inert to the action of Grignard reagents.

📜 SIMILAR VOLUMES

ChemInform Abstract: The Stereochemistry
ChemInform Abstract: The Stereochemistry of the Grignard -Ortho Ester Reaction Revisited: Regioselective Endocyclic Cleavage in the Reaction of Grignard Reagents with cis-2-Methoxy-4-methyl-1,3-dioxane.
✍ W. F. BAILEY; A. A. CROTEAU; A. D. RIVERA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 29 KB 👁 2 views

The Stereochemistry of the Grignard -Ortho Ester Reaction Revisited: Regioselective Endocyclic Cleavage in the Reaction of Grignard Reagents with cis-2-Methoxy-4-methyl-1,3-dioxane. -cis-Dioxane (Ia) selectively reacts with Grignard reagents (cf. (II)) via rupture of the less congested C(2)-O(1) bo