By cyclodehydration to centropolyindanes: Development of a novel class of indane hydrocarbons with three-dimensional molecular frameworks using a classical synthetic tool

Kuck D (1996)
SYNLETT (10): 949-&.

Journal Article | Published | English

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Abstract
Cyclodehydration of suitably 2-benzyl-substituted indan-1-ols and indan-1-ones and related compounds is a key synthetic tool for the highly efficient construction of three-dimensional carbocyclic frameworks containing several centrically condensed indane units. Inspired by a fortuitous cyclodehydration observed as a side reaction, this investigation has been spanned from two-fold cyclodehydration of 19-indanediols to ''bicyclodehydration'' of 1-indanones and 1,3-indanediones and to some directed applications of cyclodehydration of C-s-diindanols, C-s-diindanones, and C-s-diindanolones with sterically preoriented phenyl groups. Benzo-anellated triquinacenes and fenestranes, in particular, have become directly accessible by two-fold cyclodehydration, the latter including all-cis- but also cis,cis,cis,trans-fenestrane stereoisomers. Notwithstanding some limits of the strategy, the broad applicability of two-fold pentaannulation by cyclodehydration has led to the development of an entire class of novel polycyclic hydrocarbons, the ''centropolyindanes''.
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Kuck D. By cyclodehydration to centropolyindanes: Development of a novel class of indane hydrocarbons with three-dimensional molecular frameworks using a classical synthetic tool. SYNLETT. 1996;(10):949-&.
Kuck, D. (1996). By cyclodehydration to centropolyindanes: Development of a novel class of indane hydrocarbons with three-dimensional molecular frameworks using a classical synthetic tool. SYNLETT(10), 949-&.
Kuck, D. (1996). By cyclodehydration to centropolyindanes: Development of a novel class of indane hydrocarbons with three-dimensional molecular frameworks using a classical synthetic tool. SYNLETT, 949-&.
Kuck, D., 1996. By cyclodehydration to centropolyindanes: Development of a novel class of indane hydrocarbons with three-dimensional molecular frameworks using a classical synthetic tool. SYNLETT, (10), p 949-&.
D. Kuck, “By cyclodehydration to centropolyindanes: Development of a novel class of indane hydrocarbons with three-dimensional molecular frameworks using a classical synthetic tool”, SYNLETT, 1996, pp. 949-&.
Kuck, D.: By cyclodehydration to centropolyindanes: Development of a novel class of indane hydrocarbons with three-dimensional molecular frameworks using a classical synthetic tool. SYNLETT. 949-& (1996).
Kuck, Dietmar. “By cyclodehydration to centropolyindanes: Development of a novel class of indane hydrocarbons with three-dimensional molecular frameworks using a classical synthetic tool”. SYNLETT 10 (1996): 949-&.
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