137343-66-9

Upstream product

• 108-86-1 bromobenzene 
• 56447-09-7 2,2-dichloro-1-methyl-cyclopropanoyl chloride 
• 1447-14-9 2,2-dichloro-1-methylcyclopropanecarboxylic acid 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 40808-46-6 4-methyl-2,5-diphenylthiophene, 

Relevant academic research and scientific papers

Regiocontrolled benzannulation of diaryl(gem-dichlorocyclopropyl)methanols for the synthesis of unsymmetrically substituted α-arylnaphthalenes: Application to total synthesis of natural lignan lactones

(Chemical Equation Presented) An efficient synthesis of highly substituted α-arylnaphthalene analogues has been developed utilizing Lewis acid-promoted regiocontrolled benzannulation of aryl(aryl′)-2,2- dichlorocyclopropylmethanols (aryl ≠ aryl′; abbrevia

Sequential and regioselective Friedel-Crafts reactions of gem-dihalogenocyclopropanecarbonyl chlorides with benzenes for the synthesis of 4-aryl-1-naphthol derivatives

Novel, sequential and regioselective Friedel-Crafts type reactions of (E)-3-aryl-2,2-dihalogenocyclopropanecarbonyl chlorides 1 and 2,2-dichlorocyclopropanecarbonyl chlorides 3 with benzenes produce various 4-aryl-3-halogeno-1-naphthols 2 and 4-aryl-1-naphthols 4, respectively. One of the benzannulations involves the intramolecular cyclization of acid chlorides 1, followed by intermolecular coupling with substituted benzenes to give 4-aryl-3-halogeno-1-naphthols 2. As a demonstration of this annulation, 4-aryl-3-bromo-1-naphthols 2i and 2k are successfully converted into new analogues of 1-aryl-3-hydroxymethyl-4-methoxy-2-naphthoic acid lactones 13, a class of lignan lactones. The other benzannulation involves three series of reactions using acid chlorides 3a-c: (1) the intermolecular Friedel-Crafts acylation of 3 with one benzene molecule giving the intermediary 2,2-dichlorocyclopropyl(phenyl)-methanones 14a-c; (2) the intermolecular trapping of 14a-c with another benzene molecule accompanied by regioselective ring opening; and (3) the final intramolecular cyclization giving 4-phenyl-1-naphthols 4a-c. The use of p-xylene also gives the corresponding 4-(p-xylyl)-1-naphthol 4d. The reactions of alternatively prepared ketones 14 with benzenes gives a variety of 'unsymmetrically' substituted 4-aryl-1-naphthols 4c,e-k under identical conditions. However, the reaction using p-methoxyphenyl ketone analogues 14g does not produce 4-aryl-1-naphthols, but gives 5-aryl-2-(p-methoxyphenyl)-3-methylfurans 16. These annulations proceed straightforwardly (in a one-pot manner) and this variation is due to the highly regioselective cyclopropane ring-openings.

Regiocontrolled benzannulation of diaryl(gem-dichlorocyclopropyl)methanols for the synthesis of 'unsymmetrically' substituted α-arylnaphthalenes

Aryl1 (aryl2)(gem-dichlorocyclopropyl)methanol 1 underwent alternative benzannulation to give 'unsymmetrically' substituted 1-(aryl1)-4-chloronaphthalenes 2/A catalyzed by SnCl4 or TiCl4 and to give 1

Novel method for the synthesis of α- and β-halogenonaphthalenes by regioselective benzannulation of aryl(gem-dihalogenocyclopropyl)methanols: Application to the total synthesis of the lignan lactones, justicidin E and taiwanin C

Acid treatment of two types of aryl(gem-dihalogenocyclopropyl)methanols (ADCMs) 1 and 3 gives α- and β-halogenonaphthalenes in good yields with excellent selectivity. These alternative annulations involve two distinctive types of highly regioselective acid-induced cyclopropane ring cleavage, wherein the preferential formation of more stable cationic intermediates determines the selectivity. The stereochemical mode of both the preparation and the annulation between diastereoisomers of an ADCM has been checked. As a demonstration of this annulation, a total synthesis of each of the natural lignan lactones, justicidin E 19 and taiwanin C 20, has also been performed. Since these 4-arylnaphthalenes are expected to exhibit biological activity, the anti-platelet activating factor (anti-PAF) activity of justicidin E has been assayed.

Sequential and regioselective Friedel-Crafts reactions of gem-dihalocyclopropanecarbonyl chlorides with benzenes for the synthesis of 4-aryl-1-naphthol derivatives

Two types of novel, sequential and regioselective Friedel-Crafts reactions of gem-dihalocyclopropanecarbonyl chlorides with benzenes proceeded in a one-pot manner; E-3-aryl-2,2-dihalo-cyclopropanecarbonyl chlorides reacted with substituted benzenes to afford 4-aryl-3-halo-1-naphthols, while 2,2-dichlorocyclopropanecarbonyl chlorides were transformed into 4-aryl-1-naphthols in benzene or p-xylene. Both annulations involved alternative and highly regioselective cyclopropane ring-openings.