<b>The Effects of Ring Size on the Rates of Acid- and Base-catalyzed Enolization of Homologous Cycloalkanones and Cycloalkyl Phenyl Ketones</b>

Shechter, Harold; Collis, Michael J.; Dessy, Raymond E.; Okuzumi, Yuzi.; Chen, Alan.

doi:10.1021/ja00874a012

Cited by 47 publications

(22 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In agreement with previous work with dibenzylideneacetone (22)." monosulfonation of 2,5-dibenzylidenecyclopentanone (2) was possible because the carbonyl group was initially protonated (32) in the highly acidic medium (Scheme I).…”

supporting

confidence: 90%

The Synthesis and Chlorosulfonation of Some Diarylidene and Heteroarylidene Ketones With Varying Alicyclic Ring Size

Cremlyn

Frearson

Graham

1995

Phosphorus, Sulfur, and Silicon and the Related Elements

View full text Add to dashboard Cite

A series of diarylidene and heteroarylidene ketones (1-20) was prepared using alicyclic ketones ((CH,)nC=O where n = 3 to 7). An improved synthesis of 2,4-dibenzylidenecyclobutanone (1) is described and the ease of preparation of the arylidene derivatives is considered in terms of the size of the alicyclic ring. Treatment of 2,5-dibenzylidenecyclopentanone (2) with chlorosulfonic acid (10 mole equivalents) afforded the 4,4'-bis-sulfonyl chloride (23). reducing the amount of chlorosulfonic acid (6 mole equivalents) produced the corresponding mono-sulfonyl chloride (24). Only the respective 4.4'-bis-sulfonyl chlorides (39, 45, 51) could be isolated from the diarylidene ketones derived from larger alicyclic rings. Attempted chlorosulfonation of 2.4-dibenzylidene cyclobutanone (1) gave a mixture of products which could not be clearly characterised. The sulfonyl chlorides were converted into stable sulfonamides (25-29, 35, 36, 38. 40-44, 46-48, 52, 54) by condensation with amines, and selected samples were screened for biological activity as potential insecticides, herbicides and fungicides. The orientation of sulfonation is discussed in relation to stereoelectronic factors and the relevant spectral data.

show abstract

supporting

confidence: 90%

The Synthesis and Chlorosulfonation of Some Diarylidene and Heteroarylidene Ketones With Varying Alicyclic Ring Size

Cremlyn

Frearson

Graham

1995

Phosphorus, Sulfur, and Silicon and the Related Elements

View full text Add to dashboard Cite

show abstract

“…During the aldol reaction, cycloheptanone showed a weak reactivity compared to cyclopentanone and cyclohexanone; the relative rate of enol formation decreasing drastically with the increasing ring size. 9 Classically, the aldol reaction may be catalyzed by acids or bases, the latter being more frequently employed in spite of the fact that a method has been described with the use of bis(4-methoxyphenyl) telluroxide (BMPTO) 10, 11 as catalyst.…”

Section: Chemistrymentioning

confidence: 99%

Total synthesis and radiolabelling of an efficient rt-PA inhibitor: [11C] (Z,Z)-BABCH. A first route to [11C] labelled amidines

Siméon

Sobrio

Gourand

et al. 2001

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

“…De plus, Schechter et al [7] ont trouvk que la constante de vitesse de bromation de la cyclohexanone est d'environ 5 fois suptrieure a celle de la cyclopentanone.…”

Section: -unclassified

Réactions chimiques oscillantes III. Effets de la température et de la composition chimique sur la «période d'induction» des systèmes BrO/Ce⁴⁺/Cyclohexanone et BrO/Ce⁴⁺/Cyclopentanone

Farage

Janjic

1980

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

The Effects of Ring Size on the Rates of Acid- and Base-catalyzed Enolization of Homologous Cycloalkanones and Cycloalkyl Phenyl Ketones

Cited by 47 publications

References 1 publication

The Synthesis and Chlorosulfonation of Some Diarylidene and Heteroarylidene Ketones With Varying Alicyclic Ring Size

The Synthesis and Chlorosulfonation of Some Diarylidene and Heteroarylidene Ketones With Varying Alicyclic Ring Size

Total synthesis and radiolabelling of an efficient rt-PA inhibitor: [11C] (Z,Z)-BABCH. A first route to [11C] labelled amidines

Réactions chimiques oscillantes III. Effets de la température et de la composition chimique sur la «période d'induction» des systèmes BrO/Ce⁴⁺/Cyclohexanone et BrO/Ce⁴⁺/Cyclopentanone

Contact Info

Product

Resources

About

The Effects of Ring Size on the Rates of Acid- and Base-catalyzed Enolization of Homologous Cycloalkanones and Cycloalkyl Phenyl Ketones

Cited by 47 publications

References 1 publication

The Synthesis and Chlorosulfonation of Some Diarylidene and Heteroarylidene Ketones With Varying Alicyclic Ring Size

The Synthesis and Chlorosulfonation of Some Diarylidene and Heteroarylidene Ketones With Varying Alicyclic Ring Size

Total synthesis and radiolabelling of an efficient rt-PA inhibitor: [11C] (Z,Z)-BABCH. A first route to [11C] labelled amidines

Réactions chimiques oscillantes III. Effets de la température et de la composition chimique sur la «période d'induction» des systèmes BrO/Ce4+/Cyclohexanone et BrO/Ce4+/Cyclopentanone

Contact Info

Product

Resources

About

Réactions chimiques oscillantes III. Effets de la température et de la composition chimique sur la «période d'induction» des systèmes BrO/Ce⁴⁺/Cyclohexanone et BrO/Ce⁴⁺/Cyclopentanone