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1, 1-Difluoro-1H-cyclopropa[a]naphthalene

✍ Scribed by Paul Müller; Huong-Can Nguyen-Thi

Book ID
102253189
Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
229 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

1, 1‐Difluorocyclopropa[a]naphthalene (1b) is prepared in three steps from 4‐bromo‐1,2‐dihydronaphthalene (7) via carbene addition, benzylic bromination and bidehydrohalogenation. Structural evidence for formation of 1b is based on ^1^H‐ and ^19^F‐NMR spectroscopy. Compound 1b is stable in solution at −30°. Upon reaction with MeOH/H^+^ it is converted to a 1:2 mixture of 1‐ and 2‐methylnaphthoate (10 and 11, respectively).

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7. Reaction of 6e and 6f with PhSeH and Pyridine. Selenoxide 6e (9.53 mg) in CH2C12 (1 ml) was reacted with PhSeH (100 mg, 0.6 mmol) and pyridine (10 pl, ca. 0.1 mmol) for 70 h at r.t. The soln. was evaporated and the residue purified by column chromatography (silica gel, CHCI,) to yield 6.6 mg of6b