The chemistry of aryllead(IV) tricarboxylates. Reaction with silyl enol ethers

1982 ◽  
Vol 35 (11) ◽  
pp. 2237 ◽  
Author(s):  
HC Bell ◽  
JT Pinhey ◽  
S Sternhell
Keyword(s):  
Thermal Decomposition ◽  
Trifluoroacetic Acid ◽  
High Yield ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Lead Compounds ◽  
Considerable Detail ◽  
Aryl Ketone

The trimethylsilyl enol ether of acetophenone (1) and p-methoxyphenyllead triacetate (2) react to give (p-methoxyphenyl)phenacyllead(IV) diacetate (4) in high yield. This plumbation reaction has been studied for a number of ketone trimethylsilyl enol ethers and aryllead triacetates, and it would appear that it is probably limited to aryl ketone trimethylsilyl enol ethers. The trifluoroacetic acid catalysed break down of these α-plumbated ketones to substituted deoxybenzoins has been examined in considerable detail. The thermal decomposition of one of the lead compounds to a deoxybenzoin derivative has also been examined.

13C magnetic resonance studies. 120. The Simmons–Smith reaction with some silyl enol ethers. Unusual ring expansions of some norcamphorsti

1985 ◽  
Vol 63 (11) ◽  
pp. 2969-2974 ◽  
Author(s):  
Arthur J. Ragauskas ◽  
J. B. Stothers
Keyword(s):  
Magnetic Resonance ◽  
Ring Expansion ◽  
Major Product ◽  
High Yield ◽  
Silyl Ether ◽  
Enol Ether ◽  
Enol Ethers ◽  
Magnetic Resonance Studies ◽  
Silyl Enol Ethers ◽  
Ring Expansions

Unexpected difficulties with Simmons–Smith cyclopropanation of the trimethylsilyl enol ether of exo-tricyclo[3.2.1.02,4]-octan-6-one led to a reexamination of this reaction with the parent norcamphor derivative which under "concentrated" conditions gave ring-expanded allylic ethers in low yield. With the tert-butyldimethylsilyl ethers, however, the allylic product is formed in high yield in the norcamphor and exo-trimethylenenorcamphor (tricyclo[5.2.1.02,6]decan-8-one) systems. The tert-butyldimethylsilyl enol ethers of bicyclo[3.2.1]octan-6-one and nopinone do not undergo ring expansion under similar conditions but the silyl ether of 3-methylenenopinol is a major product in the latter case.

Carbon-carbon bond formation in reactions of PhIO.cntdot.HBF4-silyl enol ether adduct with alkenes or silyl enol ethers

1989 ◽  
Vol 54 (11) ◽  
pp. 2605-2608 ◽  
Author(s):  
V. V. Zhdankin ◽  
M. Mullikin ◽  
Rik Tykwinski ◽  
Bruce Berglund ◽  
Ronald Caple ◽  
...  
Keyword(s):  
Bond Formation ◽  
Enol Ether ◽  
Enol Ethers ◽  
Carbon Bond ◽  
Silyl Enol Ethers ◽  
Carbon Carbon Bond ◽  
Silyl Enol Ether

An Access to Highly Enantioenriched cis-3,5-Disubstituted γ-Lactones from α-Bromoacetate and Silyl Enol Ether

2021 ◽  
Author(s):  
Ha Rim Lee ◽  
Seo Yun Kim ◽  
Min Ji Park ◽  
Yong Sun Park
Keyword(s):  
Nucleophilic Substitution ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Synthetic Strategy ◽  
Silyl Enol Ether

A novel synthetic strategy for highly enantioenriched cis-3,5-disubstituted γ-lactones has been developed by the AgOTf-promoted nucleophilic substitution of α-bromoacetates with silyl enol ethers and subsequent reductive lactonization. The utility of...

ChemInform Abstract: Carbon-Carbon Bond Formation in Reactions of PhIO·HBF4/Silyl Enol Ether Adduct with Alkenes or Silyl Enol Ethers.

ChemInform ◽  
1989 ◽  
Vol 20 (47) ◽  
Author(s):  
V. V. ZHDANKIN ◽  
M. MULLIKIN ◽  
R. TYKWINSKI ◽  
B. BERGLUND ◽  
R. CAPLE ◽  
...  
Keyword(s):  
Bond Formation ◽  
Enol Ether ◽  
Enol Ethers ◽  
Carbon Bond ◽  
Silyl Enol Ethers ◽  
Carbon Carbon Bond ◽  
Silyl Enol Ether

scholarly journals Preparation and facile addition reactions of iminium salts derived from amino ketene silyl acetal and amino silyl enol ether

RSC Advances ◽  
2020 ◽  
Vol 10 (46) ◽  
pp. 27874-27883
Author(s):  
Makoto Shimizu ◽  
Shingo Hata ◽  
Koichi Kondo ◽  
Kazuhiro Murakami ◽  
Isao Mizota ◽  
...  
Keyword(s):  
Addition Reactions ◽  
Amino Ketone ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Iminium Salts ◽  
Silyl Enol Ether ◽  
Silyl Acetals

While iminium salts generated from amino ketene silyl acetals react with silyl enol ethers, those from amino silyl enol ethers also undergo facile addition reactions to give alpha-amino ketone derivatives in good yields.

Synthesis of Mannich bases from electrochemically generated iminium salts in the presence of silyl enol ethers

1983 ◽  
Vol 61 (7) ◽  
pp. 1379-1382 ◽  
Author(s):  
Roger N. Renaud ◽  
Denis Bérubé ◽  
Campbell J. Stephens
Keyword(s):  
Tertiary Amine ◽  
Mannich Bases ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Iminium Salts ◽  
Iminium Salt ◽  
Factors Influencing ◽  
Silyl Enol Ether ◽  
Operating Potential

The formation of Mannich bases from the reaction of silyl enol ethers with N-methyl-N-mesitylmethyleniminium salt, generated by the electrochemical oxidation of N,N-dimethylmesidine, was studied. Important factors influencing the reaction are: (a) the silyl enol ether must be nucleophilic enough to react with the iminium salt and, at the same time, must be more difficult to oxidize than the tertiary amine, (b) the product of the reaction must not be oxidized at the operating potential. Examples are presented in this paper illustrating the successes and limitations of this reaction.

Photocatalytic Decarboxylative Alkylation of Silyl Enol Ether and Enamide with N-(Acyloxy)phthalimide using Ammonium Iodide

2021 ◽  
Author(s):  
Can Liu ◽  
Ni Shen ◽  
Rui Shang
Keyword(s):  
Catalytic Amount ◽  
Ammonium Iodide ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Silyl Enol Ether ◽  
Tetrabutylammonium Iodide

Enamides and silyl enol ethers were alkylated to deliver products of N-acyl imines and ketones in the presence of a catalytic amount of N-tetrabutylammonium iodide under irradiation of purple light...

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