Unusual photorearrangements of homoconjugated diacylcyclohexa-2,4-dienes

Oren, Jakob; Schleifer, Leah; Weinman, Sarah; Fuchs, Benzion

doi:10.1039/c39880000315

Cited by 10 publications

(5 citation statements)

References 2 publications

(2 reference statements)

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“…However, triplet sensitization of 76 brings about the formation of a mixture of all-cis -cyclononatrienes 78 , resulting from a ring-opening process. Quenching experiments indicated that both products 77 and 78 are formed via different triplet excited states . See Scheme .…”

Section: The Odpm Rearrangement Of Cycloalkenyl βγ-Unsaturated Ketonesmentioning

confidence: 99%

“…93 Other examples of this class of compound that undergo the rearrangement in high yield are collected in Table 11. 66,71,87,94 In some cases a high degree of stereochemical control is observed. 66,71,94 This feature has been considered before for ketones 33 71 and 35.…”

Section: The Odpm Rearrangement Of Cycloalkenyl βγ-Unsaturated Ketonesmentioning

confidence: 99%

“…66,71,87,94 In some cases a high degree of stereochemical control is observed. 66,71,94 This feature has been considered before for ketones 33 71 and 35. 66 In this context it is worth mentioning the unusual photochemical reactivity of the keto ester 76.…”

Section: The Odpm Rearrangement Of Cycloalkenyl βγ-Unsaturated Ketonesmentioning

confidence: 99%

“…66 In this context it is worth mentioning the unusual photochemical reactivity of the keto ester 76. 94 This compound undergoes diastereoselective ODPM rearrangement, on direct irradiation at 350 nm, affording 77 in 32% yield. However, triplet sensitization of 76 brings about the formation of a mixture of all-ciscyclononatrienes 78, resulting from a ring-opening process.…”

Section: The Odpm Rearrangement Of Cycloalkenyl βγ-Unsaturated Ketonesmentioning

confidence: 99%

“…Quenching experiments indicated that both products 77 and 78 are formed via different triplet excited states. 94 See Scheme 23.…”

Section: The Odpm Rearrangement Of Cycloalkenyl βγ-Unsaturated Ketonesmentioning

confidence: 99%

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Synthetic Aspects of the Di-π-methane Rearrangement

1996

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Section: The Odpm Rearrangement Of Cycloalkenyl βγ-Unsaturated Ketonesmentioning

confidence: 99%

Section: The Odpm Rearrangement Of Cycloalkenyl βγ-Unsaturated Ketonesmentioning

confidence: 99%

Section: The Odpm Rearrangement Of Cycloalkenyl βγ-Unsaturated Ketonesmentioning

confidence: 99%

Section: The Odpm Rearrangement Of Cycloalkenyl βγ-Unsaturated Ketonesmentioning

confidence: 99%

“…Quenching experiments indicated that both products 77 and 78 are formed via different triplet excited states. 94 See Scheme 23.…”

Section: The Odpm Rearrangement Of Cycloalkenyl βγ-Unsaturated Ketonesmentioning

confidence: 99%

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Synthetic Aspects of the Di-π-methane Rearrangement

1996

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Complex Carbocyclic Skeletons from Aryl Ketones through a Three‐Photon Cascade Reaction

et al. 2020

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Starting from readily available 7‐substituted 1‐indanones, products with a tetracyclo[5.3.1.01,704,11]undec‐2‐ene skeleton were obtained upon irradiation at λ=350 nm (eight examples, 49–67 % yield). The assembly of the structurally complex carbon framework proceeds in a three‐photon process comprising an ortho photocycloaddition, a disrotatory [4π] photocyclization, and a di‐π‐methane rearrangement. The flat aromatic core of the starting material is converted into a functionalized polycyclic hydrocarbon with exit vectors in three dimensions. Ring opening reactions at the central cyclopropane ring were explored, which enable the preparation of tricyclo[5.3.1.04,11]undec‐2‐enes and of tricyclo[6.2.1.01,5]undecanes.

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