A Novel Route to Geminal Dibromocyclobutanes:  Syntheses of 2-Substituted Cyclobutanone Acetals and Their Reaction with Boron Tribromide

Nordvik, Tore; Brinker, Udo H.

doi:10.1021/jo035295o

Cited by 16 publications

(15 citation statements)

References 20 publications

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“…1 H NMR (300 MHz, CDCl 3 ) δ 7.43-7.30 (m, 2H), 7.29-7.14 (m, 3H), 4.55 (tt, J = 8.3, 2.6 Hz, 1H), 3.24 (dddd, J = 17.9, 10.6, 8.3, 2.5 Hz, 1H), 3.04 (dddd, J = 17.5, 9.9, 5.1, 2.6 Hz, 1H), 2.55 (qd, J = 10.7, 4.9 Hz, 1H), 2.25 (ddt, J = 11.3, 9.8, 8.2 Hz, 1H), in accordance with literature. [37]…”

Section: -Phenylcyclobutan-1-one (3 B)mentioning

confidence: 99%

Synthesis of 2‐Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence

Koudelka

Tobrman

2021

Eur J Org Chem

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We report a novel process for the preparation of 2-substituted cyclobutanones. Such a method relies on the cross-coupling reaction of bromocyclobutenyl diethyl phosphate with either boronic acids or organozinc reagents. Dephosphorylation of the prepared 2-substituted cyclobutenyl phosphates affords 2substituted cyclobutanones. We observed that the course of the dephosphorylation reaction depends on the properties of the substituents found on the cyclobutene nucleus. The presence of groups capable of stabilizing the negative charge is necessary for ring opening of cyclobutanones. The scope of the reported process for the preparation of 2-substituted cyclobutanones has also been extended to the preparation of cyclobutenyl sulfides.

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Section: -Phenylcyclobutan-1-one (3 B)mentioning

confidence: 99%

Synthesis of 2‐Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence

Koudelka

Tobrman

2021

Eur J Org Chem

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“…[30,31] The polyhydroxy-2,3-diaryl-9H-xanthen-9-ones 13b-s were obtained in moderate to good yields (Scheme 3, Figure 1). …”

Section: Synthesesmentioning

confidence: 99%

“…EI-MS: m/z (%) = 410 [M] +· (100), 409 (53), 408 (73), 395 (18), 393 (19), 379 (10), 377 (12), 361 (18), 334 (16), 333 (46), 321 (11), 299 (31), 273 (27), 215 (10), 202 (8), 165 (12), 151 (11), 105 (14), 86 (17), 84 (26). HRMS (EI): calcd.…”

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Efficient Syntheses of New Polyhydroxylated 2,3‐Diaryl‐9H‐xanthen‐9‐ones

2009

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A large number of hydroxylated 2,3-diaryl-9H-xanthen-9-ones have been synthesised by two different approaches, starting either from 3-bromo-2-methyl-4H-chromen-4-one or from (E)-3-bromo-2-styryl-4H-chromen-4-ones. The former method involves Heck reactions between 3-bromo-2-methyl-4H-chromen-4-one and styrenes, leading to (E)-2-methyl-3-styryl-4H-chromen-4-ones; these condensed with benzaldehyde to give (E,E)-2,3-distyryl-4H-chromen-4-ones, which led to the desired 2,3-diaryl-9H-xanthen-9-ones under reflux in 1,2,4-trichlorobenzene. 3-Bromo-2-styryl-4H-chromen-4-ones were obtained either by aldol condensations between 3-bromo-2-methyl-4H-chromen-4-one and benzaldehydes, or through Baker-Venkataraman rearrangements of 2-acetylphenyl cinnamates, followed by one-pot bromination/ cyclisation with phenyltrimethylammonium tribromide. The 2,3-diaryl-9H-xanthene-9-ones were obtained in one-pot transformations involving Heck reactions between (E)-3-

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“…6 Recently, Nordvik and Brinker described a novel route to geminal dibromocyclobutanes 6 that involved the treatment of the corresponding cyclobutanone acetal 5 with BBr 3 . 7 (B) Cleavage of ethers and cyclization. These tandem transformations involve the deprotection of an ether and the consequent intramolecular cyclization.…”

Section: Abstractsmentioning

confidence: 99%