๐”– Bobbio Scriptorium
โœฆ   LIBER   โœฆ

Reaction of 2-methoxy-1,3-dioxane with grignard reagents: reagent-substrate complexation and stereoelectronic control.

โœ Scribed by William F. Bailey; Allan A Croteau

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
283 KB
Volume
22
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

โœฆ Synopsis

The stereoelectronically controlled reaction of P-methoxy-1,3-dioxane (1) with Grignard reagents does not follow the course suggested by the behavior of anancomeric models for the conformational isomers of 1. Treatment of 1 with RMgX leads to the predominant formation of acid labile 3-(l'-methoxyalkoxy)-1-propanols, derived from endocyclic cleavage of the ring C-O bond, and only minor amounts of the expected 2-R-1,3-dioxanes.

๐Ÿ“œ SIMILAR VOLUMES

The stereochemistry of the Grignard โ€” Or
The stereochemistry of the Grignard โ€” Ortho ester reaction revisited: Regioselective endocyclic cleavage in the reaction of Grignard reagents with cis-2-methoxy-4-methyl-1,3-dioxane
โœ William F. Bailey; Allan A. Croteau; Alberto D. Rivera ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 304 KB

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 acti

Reactions of 1,1,3,3-tetramethylindane-2
Reactions of 1,1,3,3-tetramethylindane-2-selone with grignard and organolithium reagents
โœ Renji Okazaki; Akihiko Ishii; Naoki Inamoto ๐Ÿ“‚ Article ๐Ÿ“… 1984 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 172 KB

The title reaction afforded selenophilic, carbophilic, and reduction products depending on the kinds of the organometallic reagents and the heterophilic nature of the reaction was more conspicuous in the reaction with the selenoketone than with the corresponding thioketone.

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.
โœ W. F. BAILEY; A. A. CROTEAU; A. D. RIVERA ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 29 KB ๐Ÿ‘ 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