Photochemical synthesis of some propellanes through [2+2] cycloaddition of indeno[2,1-a]indene with several olefins

Shim, Sang Chul; Chae, Jeong Seok; Choi, Jung Hoon

doi:10.1021/jo00152a002

Cited by 6 publications

(1 citation statement)

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“…The photocycloaddition of 5,10-dihydroindeno[2,1-a]indene (Detert & Schollmeyer, 2019) has been studied by Shim (Shim et al, 1983) and Wolff (Wolff et al, 1992). Head-tohead and head-to-tail photodimers have been found in a 1: 2 ratio (Shim & Chae, 1982).…”

Section: Structure Descriptionmentioning

confidence: 99%

The head-to-head photodimer of indenoindene

2020

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Irradiation of 1-(1-benzocyclobutenylidene)benzocyclobutene gives indenoindene and its head-to-head photodimer nonacyclo[9.7.7.72,10.01,11.02,10.03,8.012,17.019,24.026,31]dotriaconta-3,5,7,12,14,16,19,21,23,26,28,30-dodecaene, C32H24. The molecule is built from four essentially planar indane units attached to an elongated cyclobutane ring. In the crystal, C—H...π interactions connect molecules into layers parallel to the bc plane.

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Section: Structure Descriptionmentioning

confidence: 99%

The head-to-head photodimer of indenoindene

2020

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Bimolecular Photochemical Reactions of the Stilbenes

Lewis

1986

Advances in Photochemistry

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[2+2] Cycloaddition

2010

Comprehensive Organic Name Reactions and Reagents

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Any process involving the breakage of two π bonds and the formation of two s bonds to form a four‐membered ring structure in general belong to [2+2] cycloaddition. There are various chemical reactions based on [2+2] cycloaddition. The cycloaddition of olefins under photochemical conditions is known as photochemical [2+2] cycloaddition and the reversion of [2+2] cycloaddition under UV irradiation referred to as [2+2] photocycloreversion. The molecules with olefinic structure are found to undergo photochemical [2+2] cycloaddition even in solid states. It has been found that in singlet [2+2] photocycloaddition, the regioselectivity and stereoselectivity are determined by the pericyclic minimum and exciple (or excimer) minimum, and the energy barrier between these two minima. The allenes and ketenes have also been found to undergo [2+2] cycloadditions. Furthermore the study finds that for cyclic olefins, as the size of carbocyclic ring decreases, double bonds are more bent and twisted, therefore, the cyclic olefins undergo the [2+2] cycloaddition thermally.

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Photochemical synthesis of some propellanes through [2+2] cycloaddition of indeno[2,1-a]indene with several olefins

Abstract: Also isolated from the column was 15 mg of a mixture of the two isomers, bringing the total yield up to 68%.

Cited by 6 publications

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The head-to-head photodimer of indenoindene

The head-to-head photodimer of indenoindene

Bimolecular Photochemical Reactions of the Stilbenes

[2+2] Cycloaddition

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