1975
DOI: 10.1021/jo00891a017
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General route to methoxy-substituted arylphosphonous dichlorides via mild Lewis acid catalysts

Abstract: Treatment of anisóles 3 with phosphorus trichloride in the presence of catalytic amounts of anhydrous stannic chloride provides a convenient route to a variety of melhoxy-substituted arylphosphonous dichlorides. Stannic chloride has been proven superior as a Friedel-Crafts catalyst for this reaction as compared to the previously reported use of aluminum chloride, ferric chloride, or zinc chloride. Substituent directive effects of polysubstituted anisóles have also been investigated.

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Cited by 41 publications
(11 citation statements)
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“…All reagents were distilled or otherwise purified prior to use. Dichloro(4‐methoxy phenyl)phosphine was prepared according to a literature procedure 44. Tetrahydrofuran (THF) and toluene were dried over and distilled from sodium/benzophenone prior to use.…”
Section: Methodsmentioning
confidence: 99%
“…All reagents were distilled or otherwise purified prior to use. Dichloro(4‐methoxy phenyl)phosphine was prepared according to a literature procedure 44. Tetrahydrofuran (THF) and toluene were dried over and distilled from sodium/benzophenone prior to use.…”
Section: Methodsmentioning
confidence: 99%
“…Based on this precedent, we decided to see if this type of reaction could be used to prepare either 5 or 6. [28][29][30][31] The reaction of 2,2′-bithiophene with PCl 3 using SnCl 4 as the Lewis acid catalyst was much faster than the reaction of thiophene with PCl 3 . As shown in Fig.…”
Section: Syntheses Of Phosphonate-substituted Bithiophene Derivativesmentioning
confidence: 99%
“…Also the corresponding 2-anisyldichlorophosphine (2) is prepared using the same method. Additionally, eight new phosphines (3)(4)(5)(6)(7)(8)(9)(10) are synthesized from 2-anisyl-and 2-thioanisyldichlorophosphines.…”
Section: Introductionmentioning
confidence: 99%