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Molecules 2014, 19(8), 11056-11076; doi:10.3390/molecules190811056

Bifunctionalized Allenes. Part XV. Synthesis of 2,5-dihydro-1,2-oxaphospholes by Electrophilic Cyclization Reaction of Phosphorylated α-Hydroxyallenes

Department of Organic Chemistry & Technology, Faculty of Natural Sciences, Konstantin Preslavsky University of Shumen, 115, Universitetska str., BG-9712 Shumen, Bulgaria
These authors contributed equally to this work.
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Received: 2 July 2014 / Revised: 21 July 2014 / Accepted: 23 July 2014 / Published: 29 July 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

This paper discusses a reaction of phosphorylated α-hydroxyallenes with protected or unprotected hydroxy groups involving 5-endo-trig cyclizations. Various electrophilic reagents such as sulfuryl chloride, bromine, benzenesulfenyl and benzeneselenenyl chlorides have been applied. The paper describes the reaction of 1-hydroxyalkyl-1,2-dienephosphonates with electrophiles that produces 2-methoxy-2-oxo-2,5-dihydro-1,2-oxaphospholes due to the participation of the phosphonate neighbouring group in the cyclization. On the other hand, (1E)-alk-1-en-1-yl phosphine oxides were prepared as mixtures with 2,5-dihydro-1,2-oxaphosphol-2-ium halides in a ratio of about 1:2 by chemo-, regio, and stereoselective electrophilic addition to the C2-C3-double bond in the allene moiety and subsequent concurrent attack of the external (halide anion) and internal (phosphine oxide group) nucleophiles. The paper proposes a possible mechanism that involves cyclization and additional reactions of the phosphorylated α-hydroxyallenes. View Full-Text
Keywords: phosphorylated α-hydroxyallenes; electrophilic cyclization; neighbouring group participation; 2,5-dihydro-1,2-oxaphospholes; (1E)-2,3-adducts phosphorylated α-hydroxyallenes; electrophilic cyclization; neighbouring group participation; 2,5-dihydro-1,2-oxaphospholes; (1E)-2,3-adducts
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MDPI and ACS Style

Ismailov, I.E.; Ivanov, I.K.; Christov, V.C. Bifunctionalized Allenes. Part XV. Synthesis of 2,5-dihydro-1,2-oxaphospholes by Electrophilic Cyclization Reaction of Phosphorylated α-Hydroxyallenes. Molecules 2014, 19, 11056-11076.

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