Investigations in the Retene Field. IX. The Synthesis of 5,6-Benzoretene and Some of its Derivatives<sup>1</sup>

Adelson, David E.; Bogert, Marston Taylor

doi:10.1021/ja01289a002

Cited by 8 publications

(6 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The combustion problem was solved by Bamberger and Hooker (19,20,21,22), who burned a mixture of the material and lead chromate in a tube packed with lead chromate. Other investigators (5,74) have found the analysis of retene derivatives to be both difficult and troublesome.…”

Section: Proof Of the Structure Of Retenementioning

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%

See 2 more Smart Citations

The Chemistry of Retene.

Adelson¹,

Bogert²

1939

Chem. Rev.

Self Cite

View full text Add to dashboard Cite

Section: Proof Of the Structure Of Retenementioning

confidence: 99%

Section: H Polynuclear Compoundsmentioning

confidence: 99%

Section: H Polynuclear Compoundsmentioning

confidence: 99%

See 1 more Smart Citation

The Chemistry of Retene.

Adelson¹,

Bogert²

1939

Chem. Rev.

Self Cite

View full text Add to dashboard Cite

“…Since Meisenheimer and Witte first reported a heterohelicene in 1903 (3), syntheses of various helicene derivatives have been reported. In the early 20th century, [4]helicene and its derivatives were synthesized, but it was unclear whether these were helical or not, and some were suggested to be helical but to racemize easily in solution (4). Newman and Wise synthesized optically stable [4]carbohelicene in the 1950s (5).…”

Section: Introductionmentioning

confidence: 99%

“…In the early 20th century, [4]helicene and its derivatives were synthesized, but it was unclear whether these were helical or not, and some were suggested to be helical but to racemize easily in solution (4). Newman and Wise synthesized optically stable [4]carbohelicene in the 1950s (5). [5]Helicene and its derivatives have also been synthesized (6), and the helical structure in the solid state was proved by X-ray crystallographic analysis (6c,d).…”

Section: Introductionmentioning

confidence: 99%

Structure and Property Diversity of Chiral Helicene Oligomers

Saito

Shigeno

Yamaguchi

2015

Encyclopedia of Polymer Science and Technology

View full text Add to dashboard Cite

alkylthio, and perfluoroalkyl groups. In addition, cyclization of helicene oligomers provides another method of obtaining diversity.A notable aspect in the diversity of helicene oligomers is that they can be connected to provide multidomain oligomers (Fig. 4). When two helicene oligomers are connected, they are referred to herein as homo-bidomain oligomers. Cyclic homo-bidomain oligomers are also conceivable. Hetero-multidomain oligomers can be obtained by connecting different structures of oligomers. Such manipulations provide a large diversity of structures.Because helicene can generate characteristic π−π interactions, helicene oligomers often form bimolecular, trimolecular, tetramolecular, and polymolecular aggregates in which homoaggregation and heteroaggregation can also occur. Such aggregates self-assemble to form fibrils, vesicles, liquid crystals, and surface monolayers. These noncovalent bonding interactions provide diversity of the structure of helicene oligmers. Diverse Properties of Helicene OligomersStructural diversity is directly related to diversity of properties, and the properties of a helicene oligomer can be varied by structural modifications. In addition, multidomain oligomers can be designed, in which properties A and B of each domain can be combined. Such compounds exhibit property A + B or even another property C, a result regarded as the "synthesis of a property or function." Aggregation and self-assembly of helicene oligomers further increase property diversity, which covers materials with a broad range of sizes from subnanometersized molecules through nano-and micrometer-sized molecular aggregates and molecular self-assemblies to macroscopic bulk materials. Helicene oligomers are sensitive to changes in the environment such as temperature, solvent, and concentration. Different properties appear in dilute solution, in concentrated Amidohelicene oligomers: (a) acylcic oligomers (P)-1 (n = 1−9) with dianiline spacer, cyclic oligomers (P)-2 (n = 1−10) with dianiline spacer, (b) acyclic oligomers (P)-3 (n = 1−9) with m-phenylene spacer, and acyclic reverse oligomers (P)-4 (n = 1−4). (c) Schematic representation of reversible change between helix dimer and random coils of (P)-3 and (P)-4. solution, in the crystalline state, in the amorphous state, on the solid surface, at the solid-liquid interface, in fiber assemblies, in liquid crystals, and in gels. Dynamic properties of helicene oligomers are also interesting, and structural changes are largely affected by the environment, providing a stimulus response or possible molecular switching materials. It is also noteworthy that the process of a structure change can produce unusual transient phenomena. Amidohelicene OligomersStudies on helicene oligomers were initiated with amide derivatives (Fig. 5a, top), in which the spacer has a bent shape and includes both hydrogen bonding donor and acceptor moieties (24). (P)-5,8-Helicenedicarboxylate was reacted with bis(2,6-dimethylanilino)cyclohexane to give a series of acyclic helicene oligomers 1 up t...

show abstract

TheClemmensen Reduction

Martin

2011

Organic Reactions

View full text Add to dashboard Cite

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.

show abstract

Investigations in the Retene Field. IX. The Synthesis of 5,6-Benzoretene and Some of its Derivatives¹

Cited by 8 publications

References 0 publications

The Chemistry of Retene.

The Chemistry of Retene.

Structure and Property Diversity of Chiral Helicene Oligomers

TheClemmensen Reduction

Contact Info

Product

Resources

About

Investigations in the Retene Field. IX. The Synthesis of 5,6-Benzoretene and Some of its Derivatives1

Cited by 8 publications

References 0 publications

The Chemistry of Retene.

The Chemistry of Retene.

Structure and Property Diversity of Chiral Helicene Oligomers

TheClemmensen Reduction

Contact Info

Product

Resources

About

Investigations in the Retene Field. IX. The Synthesis of 5,6-Benzoretene and Some of its Derivatives¹