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Photochemical Cycloaddition of Cyclobutene

IP.com Disclosure Number: IPCOM000095060D
Original Publication Date: 1965-Sep-01
Included in the Prior Art Database: 2005-Mar-07
Document File: 2 page(s) / 33K

Publishing Venue

IBM

Related People

Strinvasan, R: AUTHOR [+3]

Abstract

This relates to the cycloaddition of cyclobutene to radiation activated double bonds to provide derivatives of bicyclo ›2.2.0| hexane. The drawings show the molecular structures of the compounds. Where possible, these compounds are related to a drawing diagram by referring to the associated Roman numeral.

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Photochemical Cycloaddition of Cyclobutene

This relates to the cycloaddition of cyclobutene to radiation activated double bonds to provide derivatives of bicyclo >2.2.0| hexane. The drawings show the molecular structures of the compounds. Where possible, these compounds are related to a drawing diagram by referring to the associated Roman numeral.

The cycloaddition of cyclobutene I to activate double bonds gives derivatives of bicyclo >2.2.0| hexane II. In cases in which the activated double bond is part of a ring system, tricyclic molecules which incorporate II are realized.

In the photochemical cycloaddition of cyclobutene I to benzene III, the reaction is carried out by irradiating a 20% solution of cyclobutene in benzene at 2537A until the solution turns intensely yellow. The irradiation is interrupted, the unreacted cyclobutene is distilled off and recovered. From the residue, the benzene is evaporated to leave behind a crude mixture from which an addition compound of benzene and cyclobutene is obtained in 25% yield. The formula of this compound is C(10)H(12). The structures are IV and V on the basis of spectroscopic evidence. IV and V can be reduced with hydrogen gas in the presence of Adam's platinum oxide catalyst to give VI and VII.

In a similar fashion, the photochemical cycloaddition of 2-cyclopentenone VIII to cyclobutene is also achieved. A solution of 4g of cyclobutene and 3g of VIII in 60 ml of cyclohexane is irradiated with light of 3000 - 400...