Figure 2.

Iodo-sulfenylation of propellane 1. Yields of pure isolated products. ^aSame reaction conditions as in entry 9 of Table 1, except as otherwise noted. ^bIn acetone. ^cDIH (0.50 equiv) instead of NIS. ^dAt −10 °C for 10 min and then room temperature for 1 h. ^eOn 11.4 mmol of mercapto reagent. ^fMercapto reagent (1.5 equiv), NIS (1.1 equiv), and 1 (1.0 equiv). ^gOn 11.2 mmol of mercapto reagent. ^hMercapto reagent (1.0 equiv), NIS (1.0 equiv), and 1 (2.0 equiv).