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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)