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- W2116311719 abstract "Photolyse von 1-Isobutoxybicyclo[3.1.0]hexan-2-on-tosylhydrazon (3) in Natronlauge ergab Bicyclo[2.1.1]hexan-5-on (6) (37%). 6 wurde auch aus den 1-Isobutoxybicyclo[3.1.0]hexan-2-ol-(3,5-dinitrobenzoaten) (8b, 9b) erhalten. 1-Isobutoxybicyclo[4.1.0]heptan-2-on-tosylhydrazon (10) und die entsprechenden 3,5-Dinitrobenzoate lieferten Bicyclo[3.2.0]heptan-6-on (12) als Hauptprodukt (ca. 90%) und Bicyclo[3.1.1.]heptan-6-on (13) als Nebenprodukt (1–9%). Die Stereochemie der Abgangsgruppe hat nur einen geringen Einfluß auf diese Umlagerungen; Ionisierung und Alkylwanderung verlaufen wahrscheinlich nicht synchron. Die Solvolyse von 2-Methoxy-2-cyclohexen-1-methanol-p-toluolsulfonat (25) ergab 12 und 13 im Verhältnis 1.3:1. Deamination Reactions, 18. Rearrangements of 1-Alkoxybicyclo[n.1.0]alkane-2-diazonium Ions Photolysis of 1-isobutoxybicyclo[3.1.0]hexan-2-one tosylhydrazone (3) in aqueous sodium hydroxide afforded bicyclo[2.1.1]hexan-5-one (6) (37%). 6 was also obtained from 1-isobutoxybicyclo[3.1.0]hexan-2-ol 3,5-dinitrobenzoates (8b, 9b). 1-Isobutoxybicyclo[4.1.0]heptan-2-one tosylhydrazone (10) and the corresponding 3,5-dinitrobenzoates afforded bicyclo[3.2.0]heptan-6-one (12) as the major product (ca. 90%) and bicyclo[3.1.0]heptan-6-one (13) as the minor product (1–9%). The stereochemistry of the leaving group has only a very small effect on these arrangements, suggesting that ionization and alkyl shift are not concerted. The solvolysis of 2-methoxy-2-cyclohexene-1-methanol p-toluenesulfonate (25) produced 12 and 13 in a 1.3 : 1 ratio." @default.
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- W2116311719 date "1973-01-01" @default.
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- W2116311719 title "Desaminierungsreaktionen, 18. Umlagerung von 1‐Alkoxybicyclo[n.1.0]alkan‐2‐diazonium‐Ionen" @default.
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- W2116311719 doi "https://doi.org/10.1002/cber.19731060129" @default.
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