One‐Pot Preparation of [ n ]Ladderanes by [2π + 2π] Photocycloaddition | Zendy

Hopf Henning | Zendy; Greiving Helmut | Zendy; Beck Christian | Zendy; Dix Ina | Zendy; Jones Peter G. | Zendy; Desvergne JeanPierre | Zendy; BouasLaurent Henri | Zendy

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One‐Pot Preparation of [ n ]Ladderanes by [2π + 2π] Photocycloaddition

Author(s) -

Hopf Henning,

Greiving Helmut,

Beck Christian,

Dix Ina,

Jones Peter G.,

Desvergne JeanPierre,

BouasLaurent Henri

Publication year - 2005

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400596

Subject(s) - chemistry , polyene , photochromism , stereochemistry , computational chemistry , organic chemistry

A new method for the preparation of [ n ]ladderanes is presented, based on a one‐pot [2π+2π] photocycloaddition of [2.2]paracyclophane pseudo‐ gem bis(polyene) precursors. [3]‐ and [5]ladderanes could be isolated and were fully characterized, including their X‐ray structure analysis. The overall chemical yields from [2.2]paracyclophane as starting material were found to be 53 % ([3]ladderane) and 38 % ([5]ladderane). Preliminary investigations of their photochromic properties (reversible change from yellow or red to colourless forms) are described. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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