The Preparation of 1-Chlorocyclohexyl 4-Dimethylaminophenyl Ketone and 1-Chloro-3,3-dimethylcyclohexyl 4-Dimethylaminophenyl Ketone<sup>1</sup>

Smissman, Edward E.; Diebold, James L.

doi:10.1021/jo01023a002

Cited by 5 publications

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“…We initially sought to identify a complex scaffold upon which to examine iminium ether reactivity. To this end, a set of five multifunctional ketones 1 − 5 − were reacted with 3-azido-1-propanol under acidic conditions, followed by hydrolysis and spectroscopic analysis (Figure ) . Of these, only bicyclo[3.2.1]octanoid 5 led to an appreciable quantity of the desired lactam product.…”

Section: Resultsmentioning

confidence: 99%

Reaction Discovery Using Microfluidic-Based Multidimensional Screening of Polycyclic Iminium Ethers

et al. 2010

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Polycyclic iminium ethers are ambident electrophilic intermediates that react with a range of nucleophiles in a highly condition-dependent manner to afford densely functionalized lactams. In an effort to expand the scope of reactivity and assist in the generation of new chemotypes from these intermediates, several iminium ethers were subjected to reaction screening using an automated microfluidics reaction platform. Application of this approach led to the discovery of several interesting reaction pathways involving the iminium ether intermediates which will be described.

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Section: Resultsmentioning

confidence: 99%

Reaction Discovery Using Microfluidic-Based Multidimensional Screening of Polycyclic Iminium Ethers

et al. 2010

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Recent Applications of Optical Rotatory Dispersion and Optical Circular Dichroism in Organic Chemistry

Crabbé

1967

Topics in Stereochemistry

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Cyclopropanimine, IV α‐Bromketimine

et al. 1979

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Die Synthese von α‐Bromketiminen gelingt auf zwei Wegen, die sich ergänzen. Umsetzung der α‐Bromimidoylchloride 3 mit Grignard‐Verbindungen bei tiefer Temperatur ergibt eindeutig bezüglich der Stellung des Bromatoms in guten Ausbeuten die N‐Alkyl‐ und N‐Aryl‐α‐bromketimine 4. Das N‐(tert‐Butyl)brom‐tert‐butylketenimin 6 reagiert dagegen unerwartet unter Substitution des Broms.‐Die Bromierung der N‐tert‐Butylketimine 9, die sich von Methylketonen ableiten, mit N‐Bromsuccinimid oder 2,4,4,6‐Tetrabromcyclohexadienon erfolgt weitgehend regioselektiv an der Methylgruppe. Aus den primären Bromierungsprodukten erhält man beim Erwärmen durch (vermutlich säurekatalysierte) Isomerisierung und Disproportionierung Gleichgewichtsgemische, in denen die Bromimine 13 mit dem Bromatom an der höhersubstituierten α‐Stellung stark überwiegen.‐Das N‐tert‐Butylimin des Tetramethylcyclohexanons 10 liefert mit dem Tetrabrom‐cyclohexadienon ein Tautomerengemisch von Monobrom‐Verbindungen, mit Brom dagegen stets nur das α‐α'‐Dibromenamin 17. Aus sterischen Gründen reagiert dieses mit Protonen oder überschüssigem Brom nur noch am Stickstoff.‐Die Strukturen der Verbindungen werden durch IR‐und 1H‐NMR‐Spektren gesichert, aus denen auch Rückschlüsse auf die bevorzugte Konfiguration und Konformation abgeleitet werden.

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The Preparation of 1-Chlorocyclohexyl 4-Dimethylaminophenyl Ketone and 1-Chloro-3,3-dimethylcyclohexyl 4-Dimethylaminophenyl Ketone¹

Cited by 5 publications

References 0 publications

Reaction Discovery Using Microfluidic-Based Multidimensional Screening of Polycyclic Iminium Ethers

Reaction Discovery Using Microfluidic-Based Multidimensional Screening of Polycyclic Iminium Ethers

Recent Applications of Optical Rotatory Dispersion and Optical Circular Dichroism in Organic Chemistry

Cyclopropanimine, IV α‐Bromketimine

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The Preparation of 1-Chlorocyclohexyl 4-Dimethylaminophenyl Ketone and 1-Chloro-3,3-dimethylcyclohexyl 4-Dimethylaminophenyl Ketone1

Cited by 5 publications

References 0 publications

Reaction Discovery Using Microfluidic-Based Multidimensional Screening of Polycyclic Iminium Ethers

Reaction Discovery Using Microfluidic-Based Multidimensional Screening of Polycyclic Iminium Ethers

Recent Applications of Optical Rotatory Dispersion and Optical Circular Dichroism in Organic Chemistry

Cyclopropanimine, IV α‐Bromketimine

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The Preparation of 1-Chlorocyclohexyl 4-Dimethylaminophenyl Ketone and 1-Chloro-3,3-dimethylcyclohexyl 4-Dimethylaminophenyl Ketone¹