Save for Web... and grayscale images

I noticed a strange behavior when I use "Save for Web and Devices" on scanned BW negatives...
I import the negatives via the scanner's twain driver in Photoshop as 16bit grayscale images. My grayscale working space is normally set to the default DotGain 20% profile. When I want to show these images on the web, I use "Save for Web and Devices..." and I have selected the convert to sRGB option. For some reason, the "embed color profile" option is disabled (grayed out) when the document is in grayscale mode.
When I view the the exported image (in a color managed application or browser) it looks too dark and shadow detail is lost. Examining the file info shows that the JPG file is in RGB color space and has the sRGB profile assigned.
When I convert the image to RGB mode before I do save for web... the exported image will look exactly like it looked in Photoshop. Also, the mode change doesn't cause a change in appearance. Also, after changing to RGB, the "embed color profile" option in save for web... becomes enabled.
I experimented with other working color spaces and noticed that an image exported from a grayscale image in "GrayGamma 2.2" working color space will display almost like an image that was exported from a grayscale image converted to RGB.
I would like to understand this behavior and whether it is correct. My assumption would be that a conversion to sRGB during the export should yield the same result like a manual conversion of the image in photoshop but for some reason the results are quite different.
How can I export my grayscale images to sRGB JPG without having to convert to RGB manually while preserving the tonality from the original image?
I have attached an image which I hope might illustrate the effect I'm describing. The crop on left hand side looks as expected and is the result of exporting from an image that was converted from grayscale to RGB mode (sRGB working space) before using save for web...
The image in the middle is the result from converting to GrayGamma 2.2 color space but leaving the image in grayscale mode before saving for web and devices. It is almost identical to the crop on the left. The crop on the right hand side is the result of using save for web and devices from the original image in grayscale mode with the default DotGain 20% profile.
Thanks
/lars

These are my settings. Are they the same in your SFW dialog?

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