Investigations in the Retene Field. VIII. The Synthesis of 3'-Methyl-5,6-cyclopentenoretene

Adelson, David E.; Bogert, Marston Taylor

doi:10.1021/ja01281a053

Cited by 3 publications

(4 citation statements)

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“…8-Hydroxyretenequinone should give an intense coloration with boroacetic anhydride, but neither the Anor the B-quinone displays such behavior. The 8-position is definitely ruled out by subsequent work of Adelson and Bogert (3,4), who synthesized 3'-methyl-5,6-cyclopentenoretene from 6-acetylretene. The structure of 6-acetylretene had previously been established by these authors (1) by conversion of the ketone into the 6-retenol of Fieser and Young.…”

Section: A Hydroxy Derivativesmentioning

confidence: 99%

“…Bromination of 6-acetylretene gave 6-co-bromoacetylretene and 6-w-dibromoacetylretene (5). 6-Acetylretene was also found to undergo the Reformatsky reaction (3,4) (see below).…”

Section: LXVmentioning

confidence: 99%

Section: H Polynuclear Compoundsmentioning

confidence: 99%

“…Since retene is itself a natural product containing the methyl and isopropyl groups, two radicals which are frequently found associated in natural products and which seem to have some significant function in nature, Adelson and Bogert (3,4,5) have launched a program involving the synthesis of polynuclear hydrocarbons derived from retene. This has thus far included the synthesis of 3'-methyl-5,6-cyclopentenoretene (LXXXV) (3,4) and 5,6-benzoretene (XCII) (5). The former is of significance because it is a methyl isopropyl homolog of the Diels' hydrocarbon; the latter, 5,6-benzoretene (XCII), is of considerable interest because it is a methyl isopropyl homolog of 3,4-benzophenanthrene (42), which possesses considerable carcinogenic activity and which is the simplest carcinogenic substance yet encountered (27).…”

Section: H Polynuclear Compoundsmentioning

confidence: 99%

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The Chemistry of Retene.

Adelson¹,

Bogert²

1939

Chem. Rev.

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Section: A Hydroxy Derivativesmentioning

confidence: 99%

“…Bromination of 6-acetylretene gave 6-co-bromoacetylretene and 6-w-dibromoacetylretene (5). 6-Acetylretene was also found to undergo the Reformatsky reaction (3,4) (see below).…”

Section: LXVmentioning

confidence: 99%

Section: H Polynuclear Compoundsmentioning

confidence: 99%

Section: H Polynuclear Compoundsmentioning

confidence: 99%

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The Chemistry of Retene.

Adelson¹,

Bogert²

1939

Chem. Rev.

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TheClemmensen Reduction

Martin

2011

Organic Reactions

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The replacement of the oxygen atoms of the carbonyl group in an aldehyde or ketone by two hydrogen atoms through the use of amalgamated zinc and hydrochloric acid was first employed in 1913 by Clemmensen and is know as the Clemmensen method of reduction. The process has been applied to a large number of aldehydes and ketones as a step in the synthesis of polynuclear hydrocarbons and alkylated aromatic compounds. It has also played an important role in the elucidation of the structures of highly complex natural products. The wide use of this method has resulted in the development of several modifications of the original procedure.

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The Formation of Cyclic Ketones by IntramolecularAcylation

Johnson¹

2011

Organic Reactions

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The cyclizations of gamma‐phenylbutyric acid (I) to tetralone‐1 (II) and of beta‐phenylpropionic acid (III) to hydrindone‐1 (IV) exemplify a type of intramolecular acylation which has served as an important tool in the synthesis of polycyclic hydroaromatic and aromatic compounds, Such ring closures have been effected by a variety of methods, generally involving either the direct cyclodehydration of the acids or the cyclodehydrohalogenation of the acid chlorides by an intramolecular Freidel‐Crafts reaction. This chapter presents a discussion of these methods and the various problems involved in the formation of cyclic ketones by the ring closure of aryl‐substituted aliphatic acid.

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Investigations in the Retene Field. VIII. The Synthesis of 3'-Methyl-5,6-cyclopentenoretene

Cited by 3 publications

References 0 publications

The Chemistry of Retene.

The Chemistry of Retene.

TheClemmensen Reduction

The Formation of Cyclic Ketones by IntramolecularAcylation

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