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Photoinduced anti-markovnikov addition of methanol to alkylindenes

โœ Scribed by Harry Morrison; David Giacherio; Ganesh Pandey

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
157 KB
Volume
23
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Irradiation of acidic methanol solutions of several alkylindenes leads to anti-Markovnikov addition of the solvent to the double bond with previously reported pbotoisomerizationa virtually eliminated.

We have recently reported on two photoisomerixation reactions of alkylindenee, i.e. phototransposition (interchange of Cl and C2; cf. eq. 1) 1,2 and acid-catalyzed pbotoisomerization (of 2-alkylindenes to 2-alkylideneindanes; cf. eq. 2). 133 The tvo reactions are comhv/254 nm R2 '6"12 > (2) petitive, so that the presence of acid quenches transposition while catalyzing the double-bond migration. We now present our observations on a third mode of reaction: acid-catalyzed anti-Markovnikov addition of methanol. Several examples are presented in equations 3-5 (yields are by vpc and are based on reacted starting material; the ethers were identified by analysis of their nmr spectra and, for equations 3 and 5, by spectral comparison with independently synthesized samples).

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