1970
DOI: 10.1016/s0040-4039(01)97910-9
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A new rearrangement in the reaction of α,α-dihalocyclobutanones with base

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Cited by 29 publications
(4 citation statements)
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“…A yield of 52% was reported by Brady and Waters.66 l-Methoxy-7-chloro-eis-bicyclo[4.2.0]octan-8-one (8).6 To 1.0 g (5.2 mmol) of 7,7-dichloro-cis-bicyclo[4.2.0]octan-8-one (6) in 25 mL of refluxing methanol was added 0.34 g (6.3 mmol) of sodium methoxide. Refluxing was continued for 20 min.…”
Section: Methodsmentioning
confidence: 93%
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“…A yield of 52% was reported by Brady and Waters.66 l-Methoxy-7-chloro-eis-bicyclo[4.2.0]octan-8-one (8).6 To 1.0 g (5.2 mmol) of 7,7-dichloro-cis-bicyclo[4.2.0]octan-8-one (6) in 25 mL of refluxing methanol was added 0.34 g (6.3 mmol) of sodium methoxide. Refluxing was continued for 20 min.…”
Section: Methodsmentioning
confidence: 93%
“…Evaporative distillation (0.2 mm, 60 °C) yielded 0.29 g (35%) of product: IR (film) 1775,1100 cm-1; NMR (CCLt, 60 MHz) 2.6 (broad, -CH2CO) and 3.4 (s, -OCH3); mass spectrum m/e (rel intensity) 112 (55, M+ -CH2CO), 111 (44), 97 (56), 84 (30), 72 (26), 67 (32), 55 (55), 43 (51), 41 (100), 40 (73), 39 (61). l-(2,4,6-Trimethylbenzoxy)-7-chloro-cis-bicyclo[4.2.0]oc-tan-8-one (10).7 To an anhydrous acetone solution of 1.0 g (5.2 mmol) of 7,7-dichloro-cís-bicyclo [4.2.0] octan-8-one (6) was added a solution of 0.85 g (5.2 mmol) of 2,4,6-trimethylbenzoic acid and 0.52 g (5.2 mmol) of triethylamine in 10 mL of acetone. The reaction mixture was stirred under nitrogen for 15 min.…”
Section: Methodsmentioning
confidence: 99%
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“…As will be discussed later, this substituent orientation is explained best by an orthogonal approach of ketene to alkene; such orthogonality also accounts for the observed stereochemistry of the cycloadditions of dichloroketene to 2-cholestene and 4-tert-butylcyclohexene (6,68).…”
Section: Orientationmentioning
confidence: 90%