WITTIG-HORNER REACTION OF DIMETHYL PHTHALIDE-3-PHOSPHONATES WITH KETONES - SYNTHESIS OF 3-YLIDENEPHTHALIDES AND THEIR CONVERSION TO 2,2-DISUBSTITUTED INDAN-1,3-DIONES INCLUDING SPIROCYCLIC COMPOUNDS | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

1632799

Reference Type

Journal Article

Title

WITTIG-HORNER REACTION OF DIMETHYL PHTHALIDE-3-PHOSPHONATES WITH KETONES - SYNTHESIS OF 3-YLIDENEPHTHALIDES AND THEIR CONVERSION TO 2,2-DISUBSTITUTED INDAN-1,3-DIONES INCLUDING SPIROCYCLIC COMPOUNDS

Author(s)

Watanabe, M; Morimoto, H; Tomoda, M; Iwanaga, U

Year

1994

Is Peer Reviewed?

Journal

Synthesis
ISSN: 0039-7881
EISSN: 1437-210X

Issue

Page Numbers

1083-1086

Web of Science Id

WOS:A1994PQ02300018

Abstract

The Wittig-Horner reaction of dimethyl phthalide-3 phosphonates with various ketones was investigated under the conditions: lithium bis
(trimethylsilyl)amide (LHMDS) or sodium hydride in tetrahydrofuran, and cesium carbonate in
isopropyl alcohol. The sequential treatment of the 3-ylidenephthalides with diisobutylaluminium
hydride (DIBAL-H) and pyridinium dichromate (PDC) afforded 2,2-disubstituted indan-1,3-dione
derivatives in modest to high overall yields.

Keywords

WITTIG-HORNER REACTION; DIMETHYL PHTHALIDE-3-PHOSPHONATES; 3-YLIDENEPHTHALIDES; 2,2-DISUBSTITUTED INDAN-1,3-DIONES