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The synthesis of 4-2H-α-farnesene and 1-2H-α-farnesene

✍ Scribed by Simon Fielder; Daryl D. Rowan; Peter F. Reay

Publisher: John Wiley and Sons
Year: 1993
Tongue: French
Weight: 580 KB
Volume: 33
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580331011

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✦ Synopsis

Abstract

α‐Farnesene deuterated at C1 or C4 was synthesised by regiospecific deuteration of 2‐geranyl‐3‐methylsulpholene (2). Treatment of (2) with butyl lithium in dimethylpropenylurea (DMPU) mediated THF resulted in deprotonation at C2. Quenching with D~2~O/CH~3~CO~2~D gave a mixture of deuterated sulpholenes (43‐68%), predominantly 2‐^2^H‐2‐geranyl‐3‐methylsulpholene (5), together with bond migrated product (25‐49%). Thermal elimination of sulphur dioxide gave 4‐^2^H‐α‐farnesene (6)(85%) but with low deuterium incorporation (60%) and poor regiospecificity. Treatment of (2) with butyl lithium in TMEDA mediated THF resulted in deprotonation at C5 with minimal bond migration (1%). Quenching with D~2~O/CH~3~CO~2~D yielded 5‐^2^H‐2‐geranyl‐3‐methylsulpholene (18)(75%) which on thermolysis gave 1‐^2^H‐α‐farnesene (19)(86%) with high regiospecificity and improved deuteration (85%). Some mechanistic aspects of the alkylation of 3‐methylsulpholenes are discussed.

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