The photo-Arbuzov rearrangement of dimethyl 9-anthrylmethyl phosphite and the photodimerization of the corresponding phosphonate

Bhanthumnavin, Worawan; Ganapathy, Srinivasan; Arif, Atta M.; Bentrude, Wesley G.

doi:10.1002/(sici)1098-1071(1998)9:2<155::aid-hc10>3.0.co;2-q

Cited by 6 publications

(1 citation statement)

References 11 publications

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“…The largest lateral shift of 1.904 A ˚was observed in dimethyl 9-anthrylmethylphosphonate (CCDC refcode MAHNEO). 13 In 71 hits the lateral shifts of the p-orbitals were found to be less than this limit. Can we expect that all 71 compounds will undergo [4 + 4] photodimerization in the solid upon exposure to UV light?…”

Section: Resultsmentioning

confidence: 91%

Photodimerization of anthracene derivatives in their neat solid state and in solid molecular compounds

Zouev

Cao

et al. 2011

CrystEngComm

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The Cambridge Crystallographic Data Center provides valuable data for analysis and detection of compounds with potential to undergo photodimerization in the solid-state. Such analysis is presented for anthracene derivatives, and showed that there are many compounds that their packing in the crystal meets the requirement needed for [4 + 4] photodimerization in the solid-state. The crystal structures of various neat acyl anthracenes before and after exposure to UV light are described and the molecular structures of the dimers are compared with those obtained by exposing molecular compounds possessing a light-stable host (1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol) and light-sensitive acyl anthracenes. While exposing neat compounds to UV light causes disintegration of the single crystal, the reaction in the molecular compounds proceeds in a single-crystal to single-crystal mode until a certain rate of conversion, and then disintegrates.

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Section: Resultsmentioning

confidence: 91%

Photodimerization of anthracene derivatives in their neat solid state and in solid molecular compounds

Zouev

Cao

et al. 2011

CrystEngComm

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Michaelis‐Arbuzov Rearrangement

Bhatacharya¹

2010

Comprehensive Organic Name Reactions and Reagents

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The formation of alkyl phosphonates containing one phosphorus‐carbon bond from the reaction of an ester of trivalent phosphorus (i.e., trialkyl phosphite) and alkyl halides is generally referred to as the Michaelis–Arbuzov rearrangement. This reaction has been extensively modified, such as ruthenium‐catalyzed, metalcentered radical or photo‐Arbuzov rearrangements. The analogous rearrangements have also been observed in other thio‐derivatives, etc and known as thio‐Arbuzov reaction. This reaction has been widely used for the synthesis of a variety of phosphorus related compounds.

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ChemInform Abstract: Photo‐Arbuzov Rearrangement of Dimethyl 9‐Anthrylmethyl Phosphite and the Photodimerization of the Corresponding Phosphonate.

et al. 1998

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Photo-Arbuzov Rearrangement of Dimethyl 9-Anthrylmethyl Phosphite and the Photodimerization of the Corresponding Phosphonate.-Upon irradiation, 9-anthrylmethyl phosphite (I) efficiently undergoes the photo-Arbuzov rearrangement to give the corresponding phosphonate (II). Further irradiation of (II) in solution or in the solid phase leads to the clean formation of the centrosymmetric, head to tail, [4+4] photocycloaddition product (III) as indicated by X-ray crystallographic analysis. The photodimerization is thermally reversible. -(BHANTHUMNAVIN, W.; GANAPATHY, S.; ARIF, A. M.; BENTRUDE, W. G.; Heteroat. Chem. 9 (1998) 2, 155-160; Dep. Chem., Univ. Utah, Salt Lake City, UT 84112, USA; EN)

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The photo-Arbuzov rearrangement of dimethyl 9-anthrylmethyl phosphite and the photodimerization of the corresponding phosphonate

Cited by 6 publications

References 11 publications

Photodimerization of anthracene derivatives in their neat solid state and in solid molecular compounds

Photodimerization of anthracene derivatives in their neat solid state and in solid molecular compounds

Michaelis‐Arbuzov Rearrangement

ChemInform Abstract: Photo‐Arbuzov Rearrangement of Dimethyl 9‐Anthrylmethyl Phosphite and the Photodimerization of the Corresponding Phosphonate.

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