Synthesis and photoreactions of some spiro[cycloalkanephenalenes]

M. A. Hempenius*, J. Lugtenburg, J. Cornelisse

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

8 Citations (Scopus)

Abstract

Reaction of the phenalenyl anion (1) with 1,2‐dibromoethane, 1,4‐dibromobutane and 1,5‐dibromopentane results in the formation of (bromoalkyl)phenalene derivatives. These derivatives undergo ring closure when treated with base to spiro[cyclopropane‐1,1′‐[1H]phenalene] (2), spiro[cyclopentane‐1,1′‐[1H]phenalene] (4) and spiro[cyclohexane‐1,1′‐[1H]phenalene] (5). Reaction of 1 with 1,3‐dibromopropane gives a 1:1 mixture of 1,2,3,5‐tetrahydropyrene (3a) and 1,2,3,6‐tetrahydropyrene (3b), both of which can easily be dehydrogenated to pyrene. Photochemical reactions of spiro[cycloalkanephenalenes] 2, 4 and 5 are discussed. The introduction and photochemical opening of a spirocyclopropane ring in phenalene results in the formation of 1,2‐dihydro‐4H‐cyclopenta[cd]phenalene (6), a compound with a fused five‐membered ring. The construction of pyrene and cyclopenta[cd]phenalene skeletons starting from phenalene represents a new approach in the synthesis of polycyclic aromatic hydrocarbons and their derivatives.

Original languageEnglish
Pages (from-to)403-409
Number of pages7
JournalRecueil des Travaux Chimiques des Pays‐Bas
Volume109
Issue number7-8
DOIs
Publication statusPublished - 1990
Externally publishedYes

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