The Partial Additive Chlorination of the Benzene Ring. III. Pentachlorccyclohexene and Hexachlorocyclohexene

Kolka, Alfred J.; Orloff, Harold D.; Griffing, Margaret E.

doi:10.1021/ja01634a012

Cited by 16 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In penta-and hexachlorocyclohexene, respectively, one or both of the hydrogen atoms at the olefinic carbons have been replaced by chlorine. As in benzene tetrachloride, chlorine substituents at the saturated carbons are designated e or p on the basis of the configuration present in the corresponding saturated parent substance, hexaor heptachlorocyclohexane (163). To indicate the position of the double bond with reference to the structure of the saturated precursor, a double horizontal line is employed.…”

Section: H Cyclohexene Derivativesmentioning

confidence: 99%

“…2. Pentaand hexachlorocyclohexenes Four isomers of 1,3,4,5,6-pentachloro-l-cyclohexene (CeHeCU) and of 1,2,3,4,5,6-hexachloro-l-cyclohexene (CeH^b) have been synthesized by the partial additive chlorination of mono-and o-dichlorobenzene, respectively (163). Two isomers of the former and three of the latter compound also have been obtained by monodehydrochlorination of individual isomers of benzene hexachloride and heptachlorocyclohexane, respectively (208,209,217).…”

Section: Benzene Tetrachloridementioning

confidence: 99%

“…Employing these concepts, the monodehydrochlorination reactions of the hexa-and heptachlorocyclohexanes have been interpreted and the structures of the product penta-and hexachlorocyclohexenes elucidated (163,208,209,217). The results of these investigations, summarized in figure 9, indicate the known conformations to be as foUows: 7-CeH5Cl5 (-eeepp)L6-C6H6ClB (Teeeee), a-C6H4Cle (Teeeee), ß-0ß 401ß (ppeeee), and 7-C6H4Cl6 (ppeeee).…”

Section: Benzene Tetrachloridementioning

confidence: 99%

See 2 more Smart Citations

The Stereoisomerism of Cyclohexane Derivatives.

Orloff¹

1954

Chem. Rev.

Self Cite

View full text Add to dashboard Cite

Section: H Cyclohexene Derivativesmentioning

confidence: 99%

Section: Benzene Tetrachloridementioning

confidence: 99%

Section: Benzene Tetrachloridementioning

confidence: 99%

See 1 more Smart Citation

The Stereoisomerism of Cyclohexane Derivatives.

Orloff¹

1954

Chem. Rev.

Self Cite

View full text Add to dashboard Cite

“…The y-and a-isomers of PCCHE were obtained by both methods,l,2) and their configurations have been elucidated 3 ) by chemical and physical methods as 36/45 and 35/46, respectively. The a-and f3-isomers were obtained by the latter method 2 ) and their configurations are not yet known.…”

mentioning

confidence: 99%

Isomerization of 1,3,4,5,6-Pentachlorocyclohexene-1 Isomers in Dimethyl Sulfoxide

Kurihara

Wakamura

Nakamura

et al. 1974

Agricultural and Biological Chemistry

View full text Add to dashboard Cite

In dimethyl sulfoxide, isomerization of 1,3,4,5,6-pentachlorocyclohexene-1 isomers was studied. Exchange of the allylic chlorine was indicated by the experiments with 3GCI-labeled compounds. Isomerization at the position-3 proceeded faster than at the position-6. Initial reaction rates for the isomers decreased in the order: 34/56> 35/46 (0) > 346/5 > 356/4 ~ 36/45 (r)tt. The specific rates at the initial stages increased by increasing the initial concentration of the substrates. After a prolonged reaction, the r-isomer (36/45) was the most abundant component. The isomers of the configuration: (34/56), (346/5), and (356/4) were isolated for the first time, on which PMR studies were performed.

show abstract

Über die Oxydation der Polychlorcyclohexene

1956

View full text Add to dashboard Cite

Dime Abhandlung iet meinem verehrten Lehrer, H e m Profmein-Dr. K . Freudenberg, zu eeinem 70. Qehurbtage gewidmd. S . Takei. Durch energische Oxydation von Tetra-und Pentachlorcyclohexenen werden a u k 2.3.4.6-Tetrachlor-hexandisaure und a,a'-Dichlormuconsaure noch 1.2-Oxido-3.4.5.6-tetrachlor-cyclohexan mwie 2.3.4.5.6-Pentachlorcyclohexanol-(1 ) gewonnen. Aua 1.2-Oxido -3.4.5.6tetrachlorcyclohexan entateht durch Hydrolyse 3.4.5.6-Tetrachlor-cyclohexandiol-( 1.2). Die drei lctzteren Stoffe sind in der Literatur noch nicht bekannt. Die Konstellationen (engl. conformation) und die Konfigurationcn dieeer Substanzen werden diskutiert.Neuerdings haben Kolka und Mitarbb.6) aus a-Tetrachlorcyclohcxen (VII, Tafel 1, Gruppe 1) sowie aua y-Pentachlorcyclohexen (VIII, Tafel 1, Gruppe 1) durch Permanganatoxydation dieselbe Disiiure-I (Tafel2, I) gewonnen und ihre Identitiit durch Vergleich der IR-Spektren sichergestellt ; der Mkch-Schmp. ist nicht eindeutig, weil sich die Dieiiure-I bei ihrem Schmelzpunkt (269') zereetzt. I ) M. Nakajima, T. Okubo u. Y. K a t s u m u r a , Botyu Kagaku14, lO [1949]. e, M. N a k a j i m a , T. Okubo u. Y. K a t s u m u r a , Botyu Kagaku16,97 [1950].

show abstract

The Partial Additive Chlorination of the Benzene Ring. III. Pentachlorccyclohexene and Hexachlorocyclohexene

Cited by 16 publications

References 0 publications

The Stereoisomerism of Cyclohexane Derivatives.

The Stereoisomerism of Cyclohexane Derivatives.

Isomerization of 1,3,4,5,6-Pentachlorocyclohexene-1 Isomers in Dimethyl Sulfoxide

Über die Oxydation der Polychlorcyclohexene

Contact Info

Product

Resources

About