Prins Reaction

Mechanism of the Prins Reaction

Original publication	Chem. Weekb.. 1919, 16, 1510.
Reviews	Chem. Rev.. 1952, 51, 505. Comp. Org. Syn.. 1991, 2, 527. Curr. Org. Chem.. 2007, 11, 295. Synthesis. 1977, 0, 661.

Sample reactions

SnBr4

CH2Cl2

-78 °C, 10 min, 78%

SnBr4

CH2Cl2

-78 °C, 5 min, 60%

ZnBr2, Me2NH

MeCN

50 °C, 40 min, 65% (3 steps)

NBS

DMSO, H2O

10 °C, 2 h, 32%

"Also isolated was the C2-epimer which was reverted to the starting material with zinc/ammonium chloride (52 % yield)."

CH2Cl2

-23 to 0 °C, 2.5 h

TsOH

CH2Cl2

-30 °C to RT, 17 h, 65%

TsOH

CH2Cl2

-50 °C to RT, 17.5 h, 65%

CH2O

Buffer (pH = 7)

RT, 60 min, 50% (2 steps)

SnCl4

CH2Cl2

0 °C to RT, 14.5 h, 32%