Bogert synthesis

The Bogert synthesis of 2,4-diarylthiophenes consisting of the reaction of sulfur with the anils of arylalkyl ketones, has been shown to lead to a mixture of 2,4- and 2,5-disubstituted thiophenes. ... 

An alkene unit can also be used to generate a cation and cyclize to form a polycyclic aromatic compound. When 229 reacted with acetaldehyde, 230 was produced and this was cyclized by treatment with sulfuric acid to give hydronapthalene (231). This modification does not incorporate the additional ring of the cyclic ketones used in the Bogert-Cook reaction it is sometimes called the Bogert synthesis. 

A related modification also involves alkenes and is called the Darzens tetralin synthesis. 1 In this process, the alkenyl group is used directly as the eation precursor. An example is 232, which was treated with concentrated sulfurie acid followed by gentle heating to give the tetralin (tetrahydronaphthalene, 233) 8 jhe only differenee between this and the Bogert synthesis is the method by which the alkenyl arene is formed. Tetralin formation from an alkenylbenzene derivative is most often referred to as the Darzens tetralin synthesis rather than the Bogert synthesis. 

Sterhng EC, Bogert MT, The synthesis of 12-methylperhydroretene (abietane) and its non-identity with fichtelite,/ Organic Chemistry 4 20—29, 1939. 

Follow the instructions for Problem 30.26 for the foHowtng synthesis of phenanthrene (the Bogert-Cook synthesis). 

Problem 30.30 Outline a possible synthesis of chrysene by the Bogert-Cook method (Problem 30.27, p. 944), starting from naphthalene and using any aliphatic or inorganic reagents. Hint See Problem 30.7(g), p. 977.)... 

ProUem 30.31 Outline an alternative synthesis of chrysene by the Bogert-Cook methodi starting from benzene and using any aliphatic or inorganic reagents. 

Bogert-Cook synthesis. Condensation of (1-phenylethylmagnesium bromide with cyclohexanones, followed by cyclodehydration of the tertiary alcohol with concentrated sulfuric acid, with formation of octahydrophenanthrene derivatives and a small amount of spiran. 

It is a solid substance having a melting point 126-127°C and a molecular formula CigHjg. Based on the results of oxidation reactions. X-rays crystal analysis coupled with absorption spectrum measurements it was revealed that the hydrocarbon in question could be 3 -methyl-l 2-cyclopentanophenanthrene. The next essential step was to establish the structure of this compound by synthesis, e.g., that of Harper a/ (1934) who used the Bogert-Cook method commencing from ... 

Other references related to the Bogert-Cook synthesis are cited in the literature. ... 

In 1905, Bogert and Chambers described the synthesis of 32 via the acetanthranil intermediate 31, which was formed by heating 2-amino-6-nitrobenzoic acid (30) with acetic anhydride." It was reported that the yield for this reaction was nearly quantitative. This modification was compared to other variations known at that time, including heating the ammonium salt of anthranilic acid with formamide and heating the ammonium salt of N-acetylanthranilic acid, and proved to be superior. A 4-quinazolone without a substituent at the 3-position (35) has also been prepared by this method. ... 

Bodroux-Chichibabin Aldehyde Synthesis Bogert-Cook Synthesis Bohn-Schmidt Reaction... 

In 1908, aromatic polyimides were first reported by Bogert and Renstiaw [1]. Aromatic polyimides became well-known in 1950, after successful development of two-step polyimide synthesis by DuPont [2]. This class of polymers possesses a number of outstanding properties such as excellent thermal stability, mechanical strength, and electrical properties that have led to application in several fields from engineering thermoplastics to the aerospace and electronics industries, as well as for fibers and adhesives and in matrices for composite materials [3-5]. In addition, polyimides have high thermo-oxidative stability and chemical- and solvent-resistive properties, leading to many membrane-based applications... 

Much like the work conducted by the Bogert and Cook groups, the Bardhan-Sengupta synthesis of phenanthrenes helped lead to the determination of the carbon framework for steroids and was used to prepare terpene-type natural products. 

In 1933, Carston Bogert reported the synthesis of phenanthrene from either tertiary or secondary alcohol 5 or 7 via dehydration with dilute H2SO4, providing common alkene 6. Cyclization with cone. H2SO4 provided the octahydrophenanthrene 8 and ultimately dehydrogenation with elemental selenium completed the synthesis of phenanthrene 9. His group followed... 

The first synthesis of polyimides was reported by Bogert and Renshaw, who observed that, when 4-am1nophthalic anhydride or dimethyl 4-am1nophthalate is heated, water or alcohol is evolved and a polyimide is formed [1] ... 

J. Ehrlich and M. T. Bogert, J. Org. Chem. 12, 522 (1947). [The checkers recommend using concentrated HNO3 (90 mL) to H2O (10 mL) and the same conditions listed in the synthesis to obtain complete nitration to dinitroveratroL]... 

Along with aU these promising and successful early experiments, a few unsuccessful or rather unusual results were reported as well. In 1930, the American scientists Bogert and HoweUs (New York) tried to apply the photoacylation protocol to the synthesis of dibenzoylbenzohydroquinone from monobenzoy-lated 5 and benzaldehyde." However, these authors seemed to be rather skeptical of the young discipline... 

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