Electrophilic Substitution at Saturated Carbon. XVIII. Carbon as Leaving Group in Generation of Optically Active α-Sulfonylcarbanions

1963 ◽  
Vol 85 (8) ◽  
pp. 1100-1107 ◽  
Author(s):  
Donald J. Cram ◽  
Alan S. Wingrove
Keyword(s):  
Electrophilic Substitution ◽  
Optically Active ◽  
Leaving Group

The Chemistry of Metal Chelate Rings. IV. Electrophilic Substitution of Optically Active Tris-acetylacetonates

1963 ◽  
Vol 2 (3) ◽  
pp. 576-580 ◽  
Author(s):  
James P. Collman ◽  
Robert P. Blair ◽  
Roger L. Marshall ◽  
Laird Slade
Keyword(s):  
Electrophilic Substitution ◽  
Metal Chelate ◽  
Optically Active ◽  
Chelate Rings

Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution

1986 ◽  
Vol 39 (4) ◽  
pp. 563 ◽  
Author(s):  
D Young ◽  
M Jones ◽  
W Kitching
Keyword(s):  
Sulfur Dioxide ◽  
Electrophilic Substitution ◽  
Optically Active ◽  
Substitution Reactions ◽  
Cis And Trans

cis - and trans- Carvotanacetols and - piperitols have been converted into the corresponding allylic chlorides, which were made to react with both trimethyltinlithium and triphenyltinlithium . The resulting allylic stannanes were characterized by 1H, 13C and 119Sn n.m.r . spectroscopy, which permitted assignment of the relative configurations. Triphenyltinlithium appears to react in a (substantially) concerted fashion with the (optically active) chloride from the carvotanacetols yielding an optically active stannane . The corresponding trimethylstannane is optically inactive. Substitution reactions (SE′) with acid and sulfur dioxide (in chloroform) are preferentially γ-anti and specifically γ- syn respectively, in line with conclusions based on other cyclohex-2-enyl systems.

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