Photochemical reactions of trans-anethole

Nozaki, Hitosi; Otani, Ikue; Noyori, Ryoji; Kawanisi, Mituyosi

doi:10.1016/0040-4020(68)88120-7

Cited by 47 publications

(19 citation statements)

References 23 publications

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“…Recently Lewis and Kojima (7,8) used photoinitiated electron transfer sensitization (9,lO-dicyanoanthracene and other cyano aromatics) of trans-anethole to induce its dimerization, leading to qualitatively similar results to those obtained by Bauld's group (5,6). The less stable syn isomer 3 is the only product in direct photolysis of tert-anethole (7,9). Applications of the addition of 1+' to other olefins have also been reported (10).…”

Section: Introduciionsupporting

confidence: 67%

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1,3-Diketonatoboron difluoride sensitized cation radical reactions

Chow¹,

Xiang²

1991

Can. J. Chem.

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Y. L. CHOW and XIANEN CHENG. Can. J. Chem. 69, 133 1 (1991). Dibenzoylmethanatoboron difluoride (DBMBF?) and allied BF2 complexes interact from their singlet excited state with trans-anethole (t-A), quadricyclene (QC), and norbornadiene (NBD) by electron transfer to generate the corresponding cation radicals, which undergo the reported reactions. By sensitization, t-A undergoes dimerization to form the anti head-to-head and syn head-to-head dimers with retention of stereochemistry. The formation is reversible under sensitization conditions, leading to accumulation of the more stable anti isomer. However, irradiation of the absorption band of the DBMBF, -t-A ground state complex did not lead to dimerization of t-A. By DBMBF2 sensitization, QC is cleanly converted to NBD while NBD is not affected. The calculation shows QC+' possesses higher energy than NBD+' by 7.5 kcal/mol, hence an irreversible rearrangement. Other sensitizers (e.g., cyanoaromatics and tetrachlorobenzoquinone) also promote these cation radical reactions but not as cleanly as DBMBF?.

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Section: Introduciionsupporting

confidence: 67%

“…The authentic sample of the syn-3 dimer was '(AABF'--NBD+) + 3 (~~~F~--N~D f 1, which can effec-prepared by direct photolysis of 1 through a Pyrex filter (9), that of the tively retard the generation of triplet state NBD.…”

Section: Materials and Conditionsmentioning

confidence: 99%

1,3-Diketonatoboron difluoride sensitized cation radical reactions

Chow¹,

Xiang²

1991

Can. J. Chem.

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“…The thiapyrylium salt 2b was synthesized according to the procedure described by Wizinger and Ulrich. [39] The oxetanes 1a and 1b were prepared by the PaternoϪBüchi photocycloaddition of benzaldehyde and trans-β-methylstyrene [33] or trans-anethole, [40] according to literature procedures. Characterization was achieved by 1 H and 13 C NMR spectra, which were recorded with a Varian Gemini 300 spectrometer at 300 MHz and 75 MHz, respectively.…”

Section: Methodsmentioning

confidence: 99%

Electron‐Transfer Cycloreversion of 2,3‐Diaryloxetanes: Influence of the Substitution and the Photosensitizer on the Regioselectivity

Izquierdo

Miranda

2004

Eur J Org Chem

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The regioselectivity in the oxidative electron-transfer cycloreversion (CR) of 2,3-diaryloxetanes depends on the substitution of the aryl groups and on the nature of the electrontransfer photosensitizer. The reaction occurs with fragmentation of the C2−C3 and C4−O bonds either in the presence of electron-releasing substituents in the 3-aryl groups, or when chloranil is used as photosensitizer. Thus, CR of the methoxysubstituted derivative trans,trans-3-(4-methoxyphenyl)-4-methyl-2-phenyloxetane (1b) results in the production of trans-anethole and benzaldehyde. In this case, the trans-ane-

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“…Seminal work by Ledwith, 13 Bauld 14 and others 15 has demonstrated that catalytic quantities of single electron oxidants promote [2 + 2] alkene cycloaddition manifolds. Lewis 11 and others 16 have also seen success by implementing photooxidants activated by ultraviolet light.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of cyclobutane lignans via an organic single electron oxidant–electron relay system

2013

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A direct method to synthesize lignan cyclobutanes and analogs via photoinduced electron transfer is presented. A variety of oxygenated alkenes are employed to furnish terminal or substituted cyclobutane adducts with complete regiocontrol, yielding cycloadducts with trans stereochemistry. Key to minimizing competing cycloreversion is the inclusion of an aromatic electron relay (ER). This method has been adapted to the synthesis of the natural products magnosalin and pellucidin A.

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Photochemical reactions of trans-anethole

Cited by 47 publications

References 23 publications

1,3-Diketonatoboron difluoride sensitized cation radical reactions

1,3-Diketonatoboron difluoride sensitized cation radical reactions

Electron‐Transfer Cycloreversion of 2,3‐Diaryloxetanes: Influence of the Substitution and the Photosensitizer on the Regioselectivity

Synthesis of cyclobutane lignans via an organic single electron oxidant–electron relay system

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