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Synthesis 2005(7): 1109-1124
DOI: 10.1055/s-2005-861864
DOI: 10.1055/s-2005-861864
PAPER
© Georg Thieme Verlag Stuttgart · New YorkA Novel Approach to Functionalized Heterohelicenes via Chromium-Templated Benzannulation Reactions [1]
Further Information
Received
10 December 2004
Publication Date:
10 March 2005 (online)
Publication History
Publication Date:
10 March 2005 (online)
Abstract
A series of functionalized oxa- and thiaheterohelicenes has been prepared by a new progressive annulation technique based on the chromium-templated [3+2+1]benzannulation reaction of hetero[5]helicene carbene complexes with various alkynes partly in competition of angular and linear annulation. Oxidative work-up with CAN yields the respective quinones along with small amounts of nitrated products or a nitrate ester byproduct. Thermal recomplexation of an acylated monobenzannulation product by Cr(CO)6 affords the corresponding, thermodynamically favored η6-oxa[6]helicene-Cr(CO)3 complex. Bidirectional benzannulation reveals a more delicate regioselectivity and yields three different isomers including a bisquinone with an unprecedented bislinear annulation pattern. Molecular structures determined by X-ray analysis indicate a decreasing helical distortion as a result of progressive annulation, steric demand of the quinone substitution pattern (Ph>Pr>Et), or the nature of the embedded heterocycle (SO2>S>O).
Key words
chromium carbene complexes - benzannulations - oxa-/thiaheterohelicenes - quinones - arene complexes
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References
Preliminary quantum chemical calculations on electrostatic charge differences in chromium carbene starting materials and σ,π-allyl complex intermediates derived therefrom which have been performed with the semi-empirical PM3 method reveal the proper trend but were not fully conclusive. A more thorough DFT study is envisaged.