31952-55-3Relevant articles and documents
Compositions and methods for the protection of nucleophilic groups
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, (2016/01/25)
The present invention provides compositions, methods, and kits relating to the protection and deprotection of molecules comprising nucleophilic groups, such as the protection and deprotection of thermostable polymerases. Also provided are methods of performing nucleic acid amplification using polymerases protected according to the invention.
On rearrangements by cyclialkylations of arylpentanols to 2,3-dihydro-1H-indene derivatives. Part 2. An unexpected rearrangement by the acid-catalyzed cyclialkylation of 2,4-dimethyl-2-phenylpentan-3-ol under formation of trans-2,3-dihydro-1,1,2,3-tetramethyl-1H-indene
Giovannini, Edgardo,Hengartner, Urs,Pasquier, Pierre
, p. 1841 - 1849 (2007/10/03)
The acid catalyzed-cyclialkylation of 4-(2-chloro-phenyl)-2,4-dimethylpentan-2-ol (1) gave two products: 4-chloro-2,3-dihydro-1,1,3,3-tetramethyl-1H-indene (2) and also trans-4-chloro-2,3-dihydro-1,1,2,3-tetramethyl-1H-indene (3). A mechanism was proposed in Part 1 (cf. Scheme 1) for this unexpected rearrangement. This mechanism would mainly be supported by the result of the cyclialkylation of 2,4-dimethyl-2-phenylpentan-3-ol (4), which, with respect to the similarity of ion II in Scheme I and ion V in Scheme 2, should give only product 5. This was indeed the experimental result of this cyclialkylation. But the result of the cyclialkylation of 1,1,1,2′,2′,2′-hexadeuterated isomer [2H6]-4 of 4 (cf. Scheme 3) requires a different mechanism as for the cyclialkylation of 1. Such a mechanism is proposed in Schemes 5 and 6. It gives a satisfactory explanation of the experimental results and is supported by the result of the cyclialkylation of 2,4-dimethyl-3-phenylpentan-3-ol (9; Scheme 7). The alternative migration of a Ph or of an i-Pr group (cf. Scheme 6) is under further investigation.